Water → Ethyl 2-formyl-3-(1-naphthyl)propionate

HRID 903358Notes

Reaction equation

HRID 903358 reaction equation
[C:1]1([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:18](OCC)=[O:19].[H-].[Na+].O>COCCOC>[CH:18]([CH:12]([CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 10966256Ethyl 3-(1-naphthyl)propanoate

Product 1

HCID 19592256Ethyl 2-formyl-3-(1-naphthyl)propionateYield 79.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 3-(1-naphthyl)propionate (18.01 g) and ethyl formate (8.88 g) was added to a suspension of sodium hydride (57% dispersion in oil, 4.43 g) in 1,2-dimethoxyethane stirred at 5°, and the mixture was stirred at 5° for one hour and allowed to warm to room temperature. Water (300 ml) was added and the mixture was extracted with chloroform and the residual aqueous phase adjusted to pH 4 with hydrochloric acid: the mixture was extracted with ether and the extracts evaporated to give ethyl 2-formyl-3-(1-naphthyl)-propionate (16.05 g) as an oil.

Workup

  1. stirringthe mixture was stirred at 5° for one hour
  2. extractionthe mixture was extracted with chloroform
  3. extractionthe mixture was extracted with ether
  4. customthe extracts evaporated

Sources & evidence

ORD record
ord-ff562a9fffba496e9f538b41f7e8e6a6
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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