3-Hydroxybenzaldehyde → Methyl 2-(3-formylphenoxy)propanoate

HRID 432561Notes

Reaction equation

HRID 432561 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19]>CN(C)C=O>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionate

Product 1

HCID 18759681Methyl 2-(3-formylphenoxy)propanoateYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 150 ml of N,N-dimethylformamide was dissolved 10 g of 3-hydroxybenzaldehyde; 13.6 g of anhydrous potassium carbonate was added; 13.7 g of methyl 2-bromopropionate was added dropwise at room temperature under stirring and the mixture was stirred overnight at room temperature. The reaction solution was poured into ice water and the mixture was extracted twice with t-butyl methyl ether. The organic layer was washed once with 5N aqueous sodium hydroxide solution, twice with water, once with 0.1N hydrochloric acid and once with saturated aqueous sodium chloride solution in turn, dried over magnesium sulfate and then concentrated under reduced pressure to give 16.48 g of methyl 2-(3-formylphenoxy)propionate.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted twice with t-butyl methyl ether
  3. washThe organic layer was washed once with 5N aqueous sodium hydroxide solution, twice with water, once with 0.1N hydrochloric acid and once with saturated aqueous sodium chloride solution in turn
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-292efed0532c43318f663bbad203e1f9
Source dataset
uspto-grants-2003_12
Patent number
US06664214B1

Reaction notes

Loading…