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

HRID 399348

Reaktionsgleichung

Reaktionsgleichung von HRID 399348
[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]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 69240Dimethyl itaconate2×HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 15350Butanedioic acid, 2-methyl-, 1,4-dimethyl esterAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-01ee56ea5f4542ab891ac9b67fc5cba5
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817850

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