Hydrochloric Acid → Octyl p-bromomethylbenzoate

HRID 727980Notes

Reaction equation

HRID 727980 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH2:12]([OH:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C.Cl>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:20][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9571-OctanolHCID 8471TriethylamineHCID 50682894-Bromomethyl-benzoyl chloride

Product 1

HCID 19891718Octyl p-bromomethylbenzoateYield 93.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 30 ml of benzene was dissolved 2.3 g of 4-bromomethylbenzoic acid chloride, 1.37 g of n-octyl alcohol and 5 ml of triethylamine were added to the solution, and a reaction was carried out at room temperature with stirring overnight. Then, 30 ml of ethyl acetate and 10 ml of 2N HCl were added to the reaction mixture, and the organic layer was separated, washed with water and dried on magnesium sulfate. The solvent was removed by distillation, and the residue was separated and purified by the silica gel column chromatography to obtain 3.0 g of octyl 4-bromomethylbenzoate.

Workup

  1. additionwere added to the solution
  2. customwas carried out at room temperature
  3. customthe organic layer was separated
  4. washwashed with water
  5. customdried on magnesium sulfate
  6. customThe solvent was removed by distillation
  7. customthe residue was separated
  8. custompurified by the silica gel column chromatography

Sources & evidence

ORD record
ord-dc1746a67ea544129c652f250c46a658
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Reaction notes

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