CA1218381A - Preparation d'acides arylalcoylpyruviques - Google Patents

Preparation d'acides arylalcoylpyruviques

Info

Publication number: CA1218381A
Authority: CA; Canada
Prior art keywords: chloride; ethyl bromide; alkaline earth; arylalkylpyruvic; acid
Prior art date: 1983-01-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000443317A

Other languages

English (en)

Inventor

John Y. Lee

Joachim W. Wolfram

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ethyl Corp

Original Assignee

Ethyl Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-01-13

Filing date

1983-12-14

Publication date

1987-02-24

1983-01-13 Priority claimed from US06/457,520 external-priority patent/US4492798A/en

1983-12-14 Application filed by Ethyl Corp filed Critical Ethyl Corp

1987-02-24 Application granted granted Critical

1987-02-24 Publication of CA1218381A publication Critical patent/CA1218381A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 29
238000004519 manufacturing process Methods 0.000 title claims abstract 3
150000007513 acids Chemical class 0.000 title description 6
-1 alkaline earth metal salt Chemical class 0.000 claims abstract description 30
238000000034 method Methods 0.000 claims abstract description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 16
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 15
229910052751 metal Inorganic materials 0.000 claims abstract description 15
239000002184 metal Substances 0.000 claims abstract description 15
150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 12
150000001340 alkali metals Chemical class 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims abstract description 9
239000002904 solvent Substances 0.000 claims abstract description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 8
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
230000003197 catalytic effect Effects 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
239000007788 liquid Substances 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract 11
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims abstract 2
229910052799 carbon Inorganic materials 0.000 claims abstract 2
125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 20
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 16
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 8
239000000920 calcium hydroxide Substances 0.000 claims description 8
229910001861 calcium hydroxide Inorganic materials 0.000 claims description 8
235000011116 calcium hydroxide Nutrition 0.000 claims description 8
239000002585 base Substances 0.000 claims description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 claims description 4
229910021012 Co2(CO)8 Inorganic materials 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 claims description 4
STIRWWJCYONDGA-UHFFFAOYSA-N 1-(2-bromoethyl)-2,3-dimethylbenzene Chemical compound CC1=CC=CC(CCBr)=C1C STIRWWJCYONDGA-UHFFFAOYSA-N 0.000 claims description 2
QIHQCKKCEUTNJW-UHFFFAOYSA-N 1-(2-bromoethyl)-2,4-dimethylbenzene Chemical compound CC1=CC=C(CCBr)C(C)=C1 QIHQCKKCEUTNJW-UHFFFAOYSA-N 0.000 claims description 2
PZXWZXNXBNIAHO-UHFFFAOYSA-N 1-(2-bromoethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CCBr PZXWZXNXBNIAHO-UHFFFAOYSA-N 0.000 claims description 2
LAMNDTNTWLXQQP-UHFFFAOYSA-N 1-(2-bromoethyl)-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(CCBr)=C1 LAMNDTNTWLXQQP-UHFFFAOYSA-N 0.000 claims description 2
IAZCKSJRRRXZEY-UHFFFAOYSA-N 1-(2-bromoethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCBr)C=C1 IAZCKSJRRRXZEY-UHFFFAOYSA-N 0.000 claims description 2
GPHCPUFIWQJZOI-UHFFFAOYSA-N 1-(2-bromoethyl)naphthalene Chemical compound C1=CC=C2C(CCBr)=CC=CC2=C1 GPHCPUFIWQJZOI-UHFFFAOYSA-N 0.000 claims description 2
CFPQMQVLYGHEPM-UHFFFAOYSA-N 2-(2-bromoethyl)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1CCBr CFPQMQVLYGHEPM-UHFFFAOYSA-N 0.000 claims description 2
NXNNJSPCPKSLRT-UHFFFAOYSA-N 4-(2-bromoethyl)-1,2-dimethylbenzene Chemical compound CC1=CC=C(CCBr)C=C1C NXNNJSPCPKSLRT-UHFFFAOYSA-N 0.000 claims description 2
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
239000000347 magnesium hydroxide Substances 0.000 claims description 2
229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
235000012254 magnesium hydroxide Nutrition 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
STQJFINZGUXVEX-UHFFFAOYSA-N 1-(2-bromoethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CCBr)=C1 STQJFINZGUXVEX-UHFFFAOYSA-N 0.000 claims 1
SZXOBNVFLIZUAX-UHFFFAOYSA-N 2-(2-bromoethyl)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(CCBr)=C1 SZXOBNVFLIZUAX-UHFFFAOYSA-N 0.000 claims 1
229910017147 Fe(CO)5 Inorganic materials 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
150000008282 halocarbons Chemical class 0.000 description 9
PPKAIMDMNWBOKN-UHFFFAOYSA-N 2-Oxo-4-phenylbutyric acid Chemical class OC(=O)C(=O)CCC1=CC=CC=C1 PPKAIMDMNWBOKN-UHFFFAOYSA-N 0.000 description 8
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 8
229910002091 carbon monoxide Inorganic materials 0.000 description 8
238000005810 carbonylation reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
230000006315 carbonylation Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
ZQXSFZAMFNRZOQ-UHFFFAOYSA-N 2-methylpropan-2-ol;hydrate Chemical compound O.CC(C)(C)O ZQXSFZAMFNRZOQ-UHFFFAOYSA-N 0.000 description 1
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
101100353161 Drosophila melanogaster prel gene Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229940126904 hypoglycaemic agent Drugs 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA000443317A 1983-01-13 1983-12-14 Preparation d'acides arylalcoylpyruviques Expired CA1218381A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/457,520 US4492798A (en)	1982-03-01	1983-01-13	Process for preparing arylalkylpyruvic acids
US457,520		1983-01-13

Publications (1)

Publication Number	Publication Date
CA1218381A true CA1218381A (fr)	1987-02-24

Family

ID=23817059

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000443317A Expired CA1218381A (fr)	1983-01-13	1983-12-14	Preparation d'acides arylalcoylpyruviques

Country Status (2)

Country	Link
JP (1)	JPS60500445A (fr)
CA (1)	CA1218381A (fr)

1983
- 1983-11-15 JP JP59500251A patent/JPS60500445A/ja active Pending
- 1983-12-14 CA CA000443317A patent/CA1218381A/fr not_active Expired

Also Published As

Publication number	Publication date
JPS60500445A (ja)	1985-04-04

Legal Events

Date	Code	Title	Description
2004-02-24	MKEX	Expiry

Publication	Publication Date	Title
CA1263121A (fr)	1989-11-21	Carbonylation de composes renfermant des insaturations acetyleniques
US4152352A (en)	1979-05-01	Process for the carbonylation of aralkylhalides
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US4492798A (en)	1985-01-08	Process for preparing arylalkylpyruvic acids
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US4668816A (en)	1987-05-26	High yield carbonylation of halo-hydrocarbons
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EP1628946A1 (fr)	2006-03-01	Procede destine a l'hydrocarboxylation d'acides carboxyliques ethyleniquement insatures
JP2650100B2 (ja)	1997-09-03	エチリデンジアセテートの製造方法
CA1337126C (fr)	1995-09-26	Procede de preparation d'anhydrides carboxyliques cycliques
CA1205821A (fr)	1986-06-10	Preparation d'acides alpha-ceto-carboxyliques
US4435605A (en)	1984-03-06	Process for preparation of 2-phenylethyl alcohols from aromatic aldehydes
US4473706A (en)	1984-09-25	Preparation of cyclic-keto-acids
US4599435A (en)	1986-07-08	Preparation of 6-carboxy-3,4-dihydro-2H-pyran
WO1984002699A1 (fr)	1984-07-19	PROCEDE DE PREPARATION D'ACIDES alpha-CETO-CARBOXYLIQUES
US5214200A (en)	1993-05-25	Process for producing organic esters by reacting a carboxylic acid and a dialkyl ether
CA1225657A (fr)	1987-08-18	Production d'acides carboxyliques
US4544505A (en)	1985-10-01	Preparation of halo-α-keto-carboxylic acids
US4981619A (en)	1991-01-01	Process for preparing alpha-hydroxy acids
US4585889A (en)	1986-04-29	Carbonylation process for the production of monoesters aromatic dicarboxylic acids from phosphonium salts
US4948920A (en)	1990-08-14	Process for the preparation of phenylpyruvic acid from benzyl chloride
JPS5912656B2 (ja)	1984-03-24	ペンテン酸エステルの製造法