4-Hydroxybenzaldehyde → Ethyl 2-(4-formylphenoxy)acetate

HRID 579994Notes

Reaction equation

HRID 579994 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[K]>CC(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7748Ethyl bromoacetateHCID 5462222Potassium

Product 1

HCID 291358Ethyl 2-(4-formylphenoxy)acetateYield 75.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

p-Hydroxybenzaldehyde (122 g, 1 mole), ethyl bromoacetate (167 g, 1 mole), potassium carborate (138 g, 1 mole) and acetone (500 ml) were united, stirred and refluxed for 3 hours. The reaction mixture was poured into crushed ice (2 kg). The solid that separates was removed by filtrations, washed with water, dried and recrystallized from ethanol to give 157 g of product, m.p. 41°-42° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. additionThe reaction mixture was poured
  3. customThe solid that separates was removed by filtrations
  4. washwashed with water
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-114c4280e76b480da3671f9c9a580b95
Source dataset
uspto-grants-1988_06
Patent number
US04751244

Reaction notes

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