Furan → Dimethyl Succinate

HRID 1072270Notes

Reaction equation

HRID 1072270 reaction equation
[O:1]1C=C[CH:3]=[CH:2]1.[C:6]([O:14][CH3:15])(=[O:13])/[CH:7]=[CH:8]\[C:9]([O:11][CH3:12])=[O:10].[Na+].[Br-].C[O:19][C:20]1[O:24][CH2:23]CC=1OC.[CH3:27][O:28][C:29]1(OC)CCC[O:30]1>CO>[C:6]([O:14][CH3:15])(=[O:13])[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[C:7]([C:20]([O:24][CH3:23])=[O:19])([C:29]([O:28][CH3:27])=[O:30])([C:6]([O:14][CH3:15])=[O:13])[CH:8]([C:9]([O:11][CH3:12])=[O:10])[CH2:2][CH3:3].[CH3:2][O:1][CH:8]([CH2:7][C:6]([OH:14])=[O:13])[C:9]([OH:11])=[O:10]

Participants

8

Reactant 4

HCID 8029Furan2×HCID 253881Sodium BromideHCID 5271565Dimethyl maleate3×HCID 131725004HCID 131725004, compound

Product 3

HCID 7820Dimethyl SuccinateHCID 11019016Methoxysuccinic acidHCID 17783227HCID 17783227, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 500 g of electrolyte containing 9.4% of furan, 40% of dimethyl maleate, 1% of NaBr and 49.6% of methanol were electrolyzed at 19-24° C. using a current of 5 A until the charge input was 1.1 F with respect to dimethyl maleate (which corresponds to 2.4 F with respect to furan). The effluent contained the products, furan and dimethoxyfurans, in a ratio of 1.0:9.3, which corresponds to a conversion of 90%. The selectivity to dimethoxydihydrofuran/dimethoxytetrahydrofuran was 99%. Dimethyl maleate conversion was more than 99%. Tetramethyl butanetetracarboxylate and dimethyl succinate were formed in a ratio of 1:0.31 and tetramethyl butanetetracarboxylate and methoxysuccinic acid in a ratio of 1:1.15.

Workup

  1. customwere electrolyzed at 19-24° C.

Sources & evidence

ORD record
ord-dcd1d658845142d1b5f5ff2a8bf5fee4
Source dataset
uspto-grants-2005_06
Patent number
US06909016B2

Reaction notes

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