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

HRID 1899781Notes

Reaction equation

HRID 1899781 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-5e3e51b0e28a4f98b1ee175aa8007313
Source dataset
uspto-grants-1996_11
Patent number
US05573999

Reaction notes

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