Hydrogen Bromide → HCID 178447572, compound

HRID 505946Notes

Reaction equation

HRID 505946 reaction equation
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4](O)[CH2:3][CH2:2]1.[BrH:9].[C:10](Cl)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]>N1C=CC=CC=1>[C:10]([O:8][CH:1]1[CH2:2][CH2:3][CH2:4][CH:5]([Br:9])[CH2:6]1)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12].[C:10]([O:8][C@H:1]1[CH2:2][CH2:3][C@H:4]([Br:9])[CH2:5][CH2:6]1)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 111621,4-CyclohexanediolHCID 62493Pivaloyl chloride

Product 2

HCID 12171154HCID 12171154, compoundYield 12%HCID 178447572HCID 178447572, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3- and 4-bromocyclohexanols (3.6 g, 20 mmol)(the mixture of 3- and 4-bromocyclohexanols was obtained by treating 1,4-cyclohexanediol with hydrobromic acid (48 wt % in water) under reflux followed by conventional treatments) was treated with pivaloyl chloride (3.7 mL, 30 mmol) in pyridine (50 mL), which was then stirred at room temperature for 4 hours. After evaporation in vacuum, the crude mixture was purified by silica gel chromatography (hexane/ethyl acetate=20/1) to give 3-bromocyclohexyl pivaloate (trans/cis=33/67, 0.63 g, 12%) and trans-4-bromocyclohexyl pivaloate (0.79 g, 15%) as colorless oily substances.

Workup

  1. customwas obtained
  2. temperatureunder reflux
  3. customAfter evaporation in vacuum
  4. customthe crude mixture was purified by silica gel chromatography (hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-0c04129c69b14cd49912865af2a3fc2c
Source dataset
uspto-grants-2010_08
Patent number
US07781599B2

Reaction notes

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