Benzyl Alcohol → Benzyl 8-bromooctanoate

HRID 1771046

Reaction equation

HRID 1771046 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.N1(C2C=CN=CC=2)CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 5482758-Bromooctanoic acid

Product 1

HCID 11278409Benzyl 8-bromooctanoateYield 100.2%

Reagents, catalysts & solvents 2

HCID 755674-PyrrolidinopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from 8-bromooctanoic acid (2.23 g; 10.0 mmol), benzyl alcohol (1.19 g; 11.0 mmol), N,N′-dicyclohexylcarbodiimide (DCC, 2.27 g; 11.0 mmol), and 4-pyrrolidinylpyridine (50 mg) in dry dichloromethane (50 mL) using Procedure A. 3.14 g (100%) product was obtained (clear oil that eventually solidified on standing).

Sources & evidence

ORD record
ord-1387cc3a850741b1bace81194970ff9f
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Linked notes

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