Benzyl Alcohol → Benzyl 5-bromopentanoate

HRID 1771039Notes

Reaction equation

HRID 1771039 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 163685-Bromovaleric acid

Product 1

HCID 562251Benzyl 5-bromopentanoateYield 96%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

This compound was prepared from 5-bromopentanoic acid (1.81 g; 10.0 mmol), benzyl alcohol (1.62 g; 15.0 mmol), and p-toluenesulphonic acid (50 mg) in toluene (100 mL) using Procedure B. 2.60 g (96%) product was obtained (clear oil). The product was used in 8c without further purification.

Sources & evidence

ORD record
ord-baf917df42fa4adcad4ace0a445c0240
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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