Methanol → Methyl 6-Bromohexanoate

HRID 1903410Notes

Reaction equation

HRID 1903410 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:15]O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:15])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 202106-Bromohexanoic acid

Product 1

HCID 4170292Methyl 6-Bromohexanoate

Procedure

A solution of 6-bromohexanoic acid (10 g) in 50 ml of methanol to which was added 1.0 ml of concentrated sulfuric acid is heated under reflux for 8 hours. The methanol is distilled off, the residue is dissolved in ether. The ether solution is washed free of acid with water, dried over sodium sulfate and evaporated to dryness. Distillation at 0.8 mm Hg gives methyl 6-bromohexanoate, b.p. 85°-90°/0.8 mm.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 8 hours
  3. distillationThe methanol is distilled off
  4. dissolutionthe residue is dissolved in ether
  5. washThe ether solution is washed free of acid with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. distillationDistillation at 0.8 mm Hg

Sources & evidence

ORD record
ord-03a4d4feea834b28be7d1780d81dc949
Source dataset
uspto-grants-1984_03
Patent number
US04436746

Reaction notes

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