Benzyl Alcohol → Benzyl 3-oxo-5-phenylpentanoate

HRID 2198693Notes

Reaction equation

HRID 2198693 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-e593cec42fb44693b9475e1f09a4e447
Source dataset
uspto-grants-1982_11
Patent number
US04359423

Reaction notes

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