Ethanol → Ethyl 3-(4-methoxybenzoyl)propionate

HRID 1110019Notes

Reaction equation

HRID 1110019 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH2:9][CH2:10][C:11]([O:13][CH2:21][CH3:22])=[O:12])=[O:8])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 766134-Methoxy-gamma-oxobenzenebutanoic acid

Product 1

HCID 585132Ethyl 3-(4-methoxybenzoyl)propionate

Procedure

21 g of 3-(4-methoxybenzoyl)propionic acid were heated under reflux for 51/4 hours in 350 ml of ethanol after addition of 7.3 ml of concentrated sulfuric acid The reaction mixture was worked up by concentrating it, taking up the remaining residue in 100 ml of water and extracting the mixture with dichloromethane. The organic phase was separated, washed with 50 ml of saturated aqueous sodium bicarbonate solution, then washed with water until neutral, dried and concentrated. 23.3 g of crude ethyl 3-(4-methoxybenzoyl)-propionate were obtained as a yellowish, crystallizing oil.

Workup

  1. concentrationby concentrating it
  2. extractionextracting the mixture with dichloromethane
  3. customThe organic phase was separated
  4. washwashed with 50 ml of saturated aqueous sodium bicarbonate solution
  5. washwashed with water until neutral,
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b53944b32fa44caa99cf3ba0cc6fea17
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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