4-Hydroxybenzaldehyde → Methyl 2-(4-formylphenoxy)propanoate

HRID 426432Notes

Reaction equation

HRID 426432 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19]>O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionate

Product 1

HCID 18981016Methyl 2-(4-formylphenoxy)propanoateYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture consisting of 45 gm (0.37 mol) of 4-hydroxy-benzaldehyde, 111 gm (0.81 mol) of potassium carbonate, 89 ml (0.81 mol) of methyl 2-bromo-propionate and 300 ml of dimethylformanide was heated at 60° C. for 16 hours, while stirring. Thereafter, the reaction mixture was poured into 1 liter of water, and the aquous mixture was extracted with ether. The ethereal extract solution was washed with 1 N potassium hydroxide and then with water, dried and evaporated, leaving 55 gm of methyl 2-(4-formyl-phenoxy)-propionate as an oil, which was purified by passing it through a silicagel column with chloroform as the flow agent.

Workup

  1. extractionthe aquous mixture was extracted with ether
  2. extractionThe ethereal extract solution
  3. washwas washed with 1 N potassium hydroxide
  4. dry with materialwith water, dried
  5. customevaporated

Sources & evidence

ORD record
ord-35375cde96e245e5bdcaba23ecb13cff
Source dataset
uspto-grants-1979_10
Patent number
US04169720

Reaction notes

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