Methyl 3-(4-(hydroxymethyl)phenyl)propanoate → Methyl 3-(4-formylphenyl)propanoate

HRID 2227492Notes

Reaction equation

HRID 2227492 reaction equation
[OH:1][CH2:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:14]=[CH:13][C:6]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 18473826Methyl 3-(4-(hydroxymethyl)phenyl)propanoate

Product 1

HCID 11063253Methyl 3-(4-formylphenyl)propanoateYield 91.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of methyl 4-hydroxymethylhydrocinnamate (2.34 g) and manganese dioxide (21.0 g) in 40 ml dichloromethane was stirred at room temperature for 17 hours. Manganese dioxide was filtered off onto Celite. The filtrate was evaporated and dried under reduced pressure to give methyl 4-formylhydrocinnamate (2.11 g, 91%) as a colorless solid.

Workup

  1. filtrationManganese dioxide was filtered off onto Celite
  2. customThe filtrate was evaporated
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-a146bf07198c4680a4109f32c7944ebf
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

Loading…