Hydrochloric Acid → Hexanoic acid, 2-bromo-, methyl ester

HRID 487039Notes

Reaction equation

HRID 487039 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]C(Cl)=O.[CH3:10][OH:11].[CH2:12](N(CC)CC)C.Cl.[OH2:20]>C1C=CC=CC=1>[Br:1][CH:2]([CH2:3][CH2:4][CH2:5][CH3:6])[C:10]([O:20][CH3:12])=[O:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 898486-Bromohexanoyl chloride

Product 1

HCID 95578Hexanoic acid, 2-bromo-, methyl esterYield 69.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

0.3 moles of 6 bromohexanoyl chloride are dissolved in 150 ml of benzene. 26 g (0.34 moles) of methanol are added, applying cooling, and then 45 g (0.445 moles) of triethylamine in solution in 50 ml of benzene are added drop by drop. The mixture is agitated at ambient temperature for 16 hours. The reaction medium is then poured into water, acidified with HCl. The benzene is extracted. The raw product is then distilled under vacuum. This gives 43.7 g of ester with a boiling point of approx. 80° C. at a pressure of 2.25.10-2Pa of mercury; the yield is 69.7 percent.

Workup

  1. temperatureapplying cooling
  2. extractionThe benzene is extracted
  3. distillationThe raw product is then distilled under vacuum

Sources & evidence

ORD record
ord-3920ca6770f842e287dcddf6a61f82ab
Source dataset
uspto-grants-1994_03
Patent number
US05294463

Reaction notes

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