Acetic Acid → HCID 20306538, compound

HRID 1732483Notes

Reaction equation

HRID 1732483 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:17]COCC.[N+](=C)=[N-].C(O)(=O)C>C(OCC)(=O)C>[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:17])=[O:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 9550Diazomethane2×HCID 23393504-(4-Acetyl-phenoxy)-butyric acid

Product 1

HCID 20306538HCID 20306538, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(p-Acetylphenoxy)butyric acid (4.1 g.) was suspended in ethyl acetate (80 ml.), and to the suspension was added dropwise an ether solution of diazomethane with stirring under ice-cooling until a color of the diazomethane was appeared. After the stirring was continued at the same temperature for additional half an hour, a small amount of acetic acid was added to the reaction mixture, and then the solution was stirred for a while. This solution was evaporated to dryness under reduced pressure and the residue was treated with a mixture of isopropyl ether and n-hexane (1:1 by volume) to give methyl 4-(p-acetylphenoxy)butyrate (3.83 g.).

Workup

  1. waitAfter the stirring was continued at the same temperature for additional half an hour
  2. stirringthe solution was stirred for a while
  3. customThis solution was evaporated to dryness under reduced pressure
  4. additionthe residue was treated with a mixture of isopropyl ether and n-hexane (1:1 by volume)

Sources & evidence

ORD record
ord-f9b188df7d8f4a3e94ffd4df8aa503be
Source dataset
uspto-grants-1980_12
Patent number
US04237305

Reaction notes

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