Salicylaldehyde → Ethyl 1-benzofuran-2-carboxylate

HRID 2229255Notes

Reaction equation

HRID 2229255 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C.C(OCC)(=O)C>[CH2:21]([O:20][C:18]([C:17]1[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[CH:1]=1)=[O:19])[CH3:22]

Participants

6

Reactant 3

HCID 6998SalicylaldehydeHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 641368Ethyl 1-benzofuran-2-carboxylateYield 33.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of salicylaldehyde (53.10 g), K2CO3 (97 g) and ethyl bromoacetate (73.30 g) in ethanol (200 ml) was refluxed for 6 hours. The reaction mixture was diluted with ethyl acetate, washed with water, 1N NaOH and brine, dried and concentrated to give the titled compound (27.40 g) as a colorless oil

Workup

  1. temperaturewas refluxed for 6 hours
  2. washwashed with water, 1N NaOH and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae38583c3e414d89be098a3b3bb75a61
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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