Benzyl Alcohol → Benzyl 6-bromohexanoate

HRID 1771043Notes

Reaction equation

HRID 1771043 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 202106-Bromohexanoic acid

Product 1

HCID 562258Benzyl 6-bromohexanoateYield 98.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

This compound was prepared from 6-bromohexanoic acid (1.95 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. 2.80 g (98%) product was obtained (clear oil). The product was used in 9b without further purification.

Sources & evidence

ORD record
ord-2316458290ca41939801af77a54f9f4b
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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