Hexane → 3,5-Diallyl-4-hydroxybenzoic acid methyl ester

HRID 1492602

Reaction equation

HRID 1492602 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14]CC=C)[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3].C(OCC)(=O)C.[CH3:24][CH2:25][CH2:26]CCC>>[OH:14][C:13]1[C:12]([CH2:26][CH:25]=[CH2:24])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:1][CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 8058Hexane2×HCID 8857Ethyl AcetateHCID 112417484-Allyloxy-3-allylbenzoic acid methyl ester

Product 1

HCID 193856193,5-Diallyl-4-hydroxybenzoic acid methyl esterYield 97%

Procedure

The product of Step A (3.2g, 13.8 mmol) was refluxed in 12-dichlorobenzene for 3 days in the presence of a catalytic amount of BHT (10 mg). Flash column chromatography of the mixture using hexane and then 10% and 20% ethyl acetate in hexane afforded 3.1 g (97%) of the title compound.

Sources & evidence

ORD record
ord-b009125af1d046e4a898b2accff804f3
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Linked notes

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