Methanol → Methyl 6-Bromohexanoate

HRID 1719376Notes

Reaction equation

HRID 1719376 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

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

Sources & evidence

ORD record
ord-a8b4a5767a9c41f0816ef52c48dc597b
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

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