Methyl 3-bromo-5-(hydroxymethyl)benzoate → Methyl 3-bromo-5-formylbenzoate

HRID 498131Notes

Reaction equation

HRID 498131 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 11356988Methyl 3-bromo-5-(hydroxymethyl)benzoate

Product 1

HCID 11436457Methyl 3-bromo-5-formylbenzoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

In a three-necked flask with a capacity of 3 liters, 253.11 g of methyl 5-bromo-3-(hydroxymethyl)benzoate were placed and mixed with 2000 ml of toluene, and the resultant mixture was agitated to prepare a solution. The resultant solution was mixed with 44 g of manganese dioxide, and the resultant reaction mixture liquid was heated to a temperature of 105° C. and agitated for 7 hours. The resultant reaction mixture liquid was allowed to be cooled to room temperature and filtered to remove a solid fraction therefrom, and the resultant filtrate was concentrated. The target compound, methyl 5-bromo-3-formylbenzoate was obtained in an amount of 236.79 g which corresponded to a yield of 94.3%.

Workup

  1. customto prepare a solution
  2. customthe resultant reaction mixture liquid
  3. customThe resultant reaction mixture liquid
  4. temperatureto be cooled to room temperature
  5. filtrationfiltered
  6. customto remove a solid fraction
  7. concentrationthe resultant filtrate was concentrated

Sources & evidence

ORD record
ord-1b33f73222c64ca598c1322c48d07505
Source dataset
uspto-grants-2005_09
Patent number
US06949668B2

Reaction notes

Loading…