Benzyl Alcohol → Benzyl 3-oxo-5-phenylpentanoate

HRID 326196Notes

Reaction equation

HRID 326196 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)[C:18]1[CH:23]=[CH:22]C=[CH:20][CH:19]=1>C(O)C>[O:1]=[C:2]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1)=[O:5]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 61162Ethyl 3-oxo-5-phenylpentanoate

Product 1

HCID 13055807Benzyl 3-oxo-5-phenylpentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-oxo-5-phenylpentanoate (64.2 g, 0.29 mole) was heated between 190° and 210° C. under nitrogen with benzyl alcohol (28.9 ml, 0.28 mole) for 6 hours, the ethanol formed being distilled out of the reaction mixture. The resulting pale yellow oil was essentially pure product, slightly contaminated by starting materials, n.m.r. δ(CCl4) 7.23 (5H, s), 7.06 (5H, s), 5.03 (2H, s), 3.23 (2H, s) and 2.73 (4H, s).

Workup

  1. distillationbeing distilled out of the reaction mixture

Sources & evidence

ORD record
ord-f813d5d350fc4144b00499e53ec2a0bc
Source dataset
uspto-grants-1984_04
Patent number
US04444981

Reaction notes

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