Methanol → Butanedioic acid, 2-methyl-, 1,4-dimethyl ester

HRID 399348

반응식

HRID 399348 반응식
[C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[CH2:3].CO.[H][H]>CO.O1CCCC1.C(C1C=C(C(C)(C)C)C2OP([C-]3C=CC=C3)OC3C(C(C)(C)C)=CC(C(C)(C)C)=CC=3C=2C=1)(C)(C)C.[C-]1(P2OC3C(C(C)(C)C)=CC(C(C)(C)C)=CC=3C3C=C(C(C)(C)C)C=C(C(C)(C)C)C=3O2)C=CC=C1.[Fe+2]>[CH3:3][CH:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:1]([O:10][CH3:11])=[O:9]

참가 물질

6

반응물 3

HCID 887MethanolHCID 69240Dimethyl itaconate2회HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 15350Butanedioic acid, 2-methyl-, 1,4-dimethyl ester수율 99.1%

시약·촉매·용매 2

HCID 1317208751,1'-Bis[2,4,8,10-tetrakis(tert-butyl)-dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]ferrocene촉매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

A mixture of 33 mg (0.031 mmol) of the ferrocenyl bis(phosphonite) prepared in Example 1 and 12 mg (0.031 mmol) of bis(bicyclo[2.2.1]hepta-2,5-diene)rhodium(I) perchlorate in 2 mL of methanol/tetrahydrofuran (1:1) solution is stirred for two hours. Then, to the resultant solution of rhodium complex is added a solution of 490 mg (3.1 mmol) of dimethyl itaconate and 13 mL of methanol in a pressure reactor. The reactor is then pressurized to 1018 psi with hydrogen and the reaction is stirred at ambient temperature for 88 hours. 1H nmr analysis of the reaction mixtures shows a 100% conversion of dimethyl itaconate starting material to product. Workup of the reaction mixture gives 492 mg (99% yield) of desired dimethyl 2-methylsuccinate.

후처리

  1. stirringthe reaction is stirred at ambient temperature for 88 hours

출처 및 근거

ORD 기록
ord-01ee56ea5f4542ab891ac9b67fc5cba5
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817850

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