Methanol → methyl (E)-beta-methoxy-2-methylcinnamate

HRID 1735697Notes

Reaction equation

HRID 1735697 reaction equation
[CH:1]([O:6]C)([O:4][CH3:5])OC.[CH3:8][OH:9].OS(O)(=O)=O.N1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:8][O:9]/[C:17](/[C:18]1[CH:19]=[CH:18][CH:17]=[CH:16][C:19]=1[CH3:20])=[CH:16]/[C:1]([O:4][CH3:5])=[O:6]

Participants

5

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformate

Product 1

HCID 86749647methyl (E)-beta-methoxy-2-methylcinnamateYield 94%

Procedure

A mixture of 1280 g (6.7 mol) of methyl 2-methylbenzoyl acetate, 848 g (8.0 mol) of trimethyl orthoformate, 400 ml of methanol and 10 ml of concentrated H2SO4 is stirred at room temperature for 12 h. The mixture is subsequently neutralized with 20 ml of pyridine and then concentrated, and the residue is fractionally distilled (boiling point 120°-123° C./0.6 torr). 1300 g (94%) of methyl (E)-β-methoxy-2-methylcinnamate are obtained as a pale yellow oil.

Workup

  1. concentrationconcentrated
  2. distillationthe residue is fractionally distilled (boiling point 120°-123° C./0.6 torr)

Sources & evidence

ORD record
ord-7409648fc1e54629bcc22e1d32b6781b
Source dataset
uspto-grants-1996_07
Patent number
US05538940

Reaction notes

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