Ethyl formate → Ethyl 2-formyl-3-(3-methoxyphenyl)propionate

HRID 903356Notes

Reaction equation

HRID 903356 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.[CH:16](OCC)=[O:17].[Na]>CCOCC>[CH:16]([CH:10]([CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 584318Ethyl 3-(3-methoxyphenyl)propanoateHCID 5360545Sodium

Product 1

HCID 10823703Ethyl 2-formyl-3-(3-methoxyphenyl)propionateYield 40.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 3-(3-methoxyphenyl)propionate (100 g) and ethyl formate (37 g) was added dropwise to a mixture of sodium wire (11 g) in stirred ether (500 ml) at 0°. The mixture was stirred at room temperature for 16 hours and evaporated to dryness. The residue was dissolved in water and extracted with ether, the extracted aqueous phase was adjusted to pH 4 with hydrochloric acid and was extracted with ether and the ether extract was evaporated to dryness to give ethyl 2-formyl-3-(3-methoxyphenyl)propionate (46.05 g).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ether
  4. extractionwas extracted with ether
  5. extractionthe ether extract
  6. customwas evaporated to dryness

Sources & evidence

ORD record
ord-6e5f3ef0d4774b8e8b9a4313068ec3b2
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

Loading…