Benzyl Alcohol → Benzyl 11-bromoundecanoate

HRID 1771055Notes

Reaction equation

HRID 1771055 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH2:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 1781211-Bromoundecanoic acid

Product 1

HCID 289450Benzyl 11-bromoundecanoateYield 101.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

This compound was prepared from 11-bromoundecanoic acid (2.65 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. 3.62 g product was obtained, which was used in 13b without further purification.

Sources & evidence

ORD record
ord-9f0e7ea6ebaf414a8a02276eb240ab00
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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