tert-Butanol → Tert-butyl 6-bromohexanoate

HRID 974768Notes

Reaction equation

HRID 974768 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[C:10]([OH:14])([CH3:13])([CH3:12])[CH3:11]>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

3

Reactant 2

HCID 6386tert-ButanolHCID 898486-Bromohexanoyl chloride

Product 1

HCID 11550568Tert-butyl 6-bromohexanoateYield 85.8%

Procedure

6-Bromohexanoyl chloride (2 g, 9.37 mmol) was added to t-butanol (6.98 g, 93.7 mmol) under an inert atmosphere. The reaction mixture was stirred overnight and then was concentrated in vacuo, dissolved in ethyl acetate (150 ml), washed with saturated aqueous sodium bicarbonate and 10% aqueous citric acid, and dried over magnesium sulfate to yield t-butyl 6-bromohexanoate (2.02 g, 80% yield).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate (150 ml)
  3. washwashed with saturated aqueous sodium bicarbonate and 10% aqueous citric acid
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-9fb0c1ef856148dd81b2dea745bc7bf1
Source dataset
uspto-grants-1997_03
Patent number
US05607691

Reaction notes

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