Hydrochloric Acid → 7-Bromoheptanoic acid

HRID 874517Notes

Reaction equation

HRID 874517 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]CC)=[O:9].[Li+].[OH-].Cl>CCO.O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 1217237-Bromoheptanoic acidYield 96.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

to a solution of ethyl 7-bromoheptanoate (2.0 g, 8.43 mmol, 1 eq) in EtOH (15 mL) and H2O (10 mL) was added LiOH (2.0 g, 83.3 mmol, 10 eq). The mixture was stirred overnight at room temperature. The mixture was neutralized with 2N aqueous HCl with cooling in an ice-water bath, and the mixture was extracted with EtOAc. The EtOAc layer was separated, washed with water and brine, and dried over Na2SO4. Filtration and concentration in vacuo gave 1.7 g (96%) of the 7-Bromoheptanoic acid as a white solid.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. extractionthe mixture was extracted with EtOAc
  3. customThe EtOAc layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-a3494307dd0b4129a87b07c656942bc9
Source dataset
uspto-grants-2015_03
Patent number
US08980909B2

Reaction notes

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