Hydrogen Bromide → 1-Heptanol, 7-bromo-

HRID 918972Notes

Reaction equation

HRID 918972 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[BrH:10].O>C1C=CC=CC=1>[Br:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 123811,7-Heptanediol

Product 1

HCID 662841-Heptanol, 7-bromo-Yield 62%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Heptane-1,7-diol (36.0 g, 272 mmol; Alfa Aesar) and aq. 48% HBr (38 mL) were heated under reflux in benzene (400 mL) with water removal using a Dean-Stark apparatus. After 12 h, all volatiles were removed in vacuo and the residue was purified by SiO2 column chromatography using a gradient of 10-30% EtOAc/hexanes as eluent to give 7-bromoheptan-1-ol (26.22 g, 62%) as colorless oil. TLC: 50% EtOAc/hexanes, Rf≈0.4; 1H NMR (400 MHz, CDCl3) δ 3.61 (t, 2H, J=7.1 Hz), 3.39 (t, 2H, J=6.8 Hz), 1.80-1.88 (m, 2H), 1.52-1.58 (m, 2H), 1.30-1.46 (m, 6H).

Workup

  1. customall volatiles were removed in vacuo
  2. customthe residue was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-bd94c2a45a7d4a7b8b97647b4093d425
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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