Methanol → Methyl 6-Bromohexanoate

HRID 1748148Notes

Reaction equation

HRID 1748148 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:14]O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:14])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 202106-Bromohexanoic acidHCID 24386Thionyl Chloride

Product 1

HCID 4170292Methyl 6-BromohexanoateYield 100%

Procedure

Add 6-bromohexanoic acid (4.1 g, 21.1 mmol) into 100 mL absolute methanol solution and then slowly drop 30 mL thionyl chloride into the solution with an ice bath. Stir the solution at room temperature overnight, concentrate the solution and add chloroform to dissolve. After suction filtration, take and concentrate the filtrate to get the product methyl 6-bromohexanoate (4.4 g, 100%).

Workup

  1. concentrationconcentrate the solution
  2. additionadd chloroform
  3. dissolutionto dissolve
  4. filtrationAfter suction filtration
  5. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-41a4516ad5f240ce8cde8f874006c6f4
Source dataset
uspto-grants-2015_10
Patent number
US09150602B2

Reaction notes

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