Maleic Anhydride → 5,6-Dimethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione

HRID 1252684Notes

Reaction equation

HRID 1252684 reaction equation
[CH3:1][C:2]([C:4]([CH3:6])=[CH2:5])=[CH2:3].[C:7]1(=[O:13])[O:12][C:10](=[O:11])[CH:9]=[CH:8]1>C1C=CC=CC=1>[CH3:3][C:2]1[CH2:1][CH:8]2[C:7](=[O:13])[O:12][C:10](=[O:11])[CH:9]2[CH2:5][C:4]=1[CH3:6]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 105662,3-Dimethyl-1,3-butadiene

Product 1

HCID 2262975,6-Dimethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dioneYield 84.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2,3-dimethyl-1,3-butadiene (10 g; 0.122 mol), maleic anhydride (11.9 g; 0.122 mol) and benzene (30 ml) was stirred at room temperature for 10 hours, followed by removal of insoluble materials by filtration. The filtrate was concentrated under reduced pressure to give the objective compound (18.66 g). Yield, 86.6%. M.P., 73°-74° C.

Workup

  1. customfollowed by removal of insoluble materials by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e06c0e891ea84e64bc5990e652bd98a4
Source dataset
uspto-grants-1988_05
Patent number
US04745117

Reaction notes

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