Benzyl Alcohol → Benzyl 3,3-dimethylpent-4-enoate

HRID 359171Notes

Reaction equation

HRID 359171 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:19])([CH:17]=[CH2:18])[CH2:11][C:12](OCC)=[O:13].[O-]CC.[Na+]>C1(C)C=CC=CC=1>[CH3:9][C:10]([CH3:19])([CH:17]=[CH2:18])[CH2:11][C:12]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 82262Ethyl 3,3-dimethylpent-4-enoateHCID 2723922Sodium ethoxide

Product 1

HCID 13236797Benzyl 3,3-dimethylpent-4-enoateYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the manner of Example I B, 810 mg of benzyl alcohol was reacted with 1122 mg of ethyl 3,3-dimethyl-4-pentenoate in the presence of 48 mg of sodium ethoxide in 30 ml of toluene to give 1.0 g (65% yield) of benzyl 3,3-dimethyl-4-pentenoate, b.p. 92°-98°/0.1 mm.

Sources & evidence

ORD record
ord-ad9dd393d71842d6ba40c8e716cb5f05
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Reaction notes

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