Methanesulfonic Acid → Methyl (3E)-4-phenyl-3-butenoate

HRID 1858777Notes

Reaction equation

HRID 1858777 reaction equation
[CH:1](/[CH2:9][C:10]([OH:12])=[O:11])=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:13]S(O)(=O)=O.C[O-].[Na+]>CO.C(OC)(OC)OC>[C:3]1(/[CH:2]=[CH:1]/[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 53706253-Butenoic acid, 4-phenyl-, (3E)-HCID 10942334Sodium Methoxide

Product 1

HCID 5370649Methyl (3E)-4-phenyl-3-butenoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

A solution of 3.24 mg (20 mmol) of (E)-styrylacetic acid in 20 ml of methanol,2 ml of trimethyl orthoformate and 192 mg (2 mmol) of methanesulphonic acid was stirred at 50° C. under argon for one hour. For the working-up, the mixture was neutralized with 2 mmol of sodium methylate and subsequently the solvent mixture was distilled off under reduced pressure. There was obtained methyl (E)-4-phenyl-but-3-enoate as a colourless liquid in quantitative yield; MS: 176 (M)+.

Workup

  1. distillationsubsequently the solvent mixture was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1a900ae7673843fb8945ac23dcfc3053
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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