Benzyl Alcohol → Benzyl 4-bromobutanoate

HRID 736042Notes

Reaction equation

HRID 736042 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].O>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 702254-Bromobutyryl chloride

Product 1

HCID 3832489Benzyl 4-bromobutanoateYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobutyryl chloride (Aldrich Chemical Company, Wisconsin), (10.27 g, 55.4 mmol) in 100 mL of dichloromethane was added benzyl alcohol (Aldrich Chemical Company, Wisconsin), (6.29 g, 58.1 mmol), followed by potassium carbonate (8.3 g, 60 mmol) in four portions. After 2 hours, water was added, and the layers were separated. The organic layer was washed with water, brine, and dried over magnesium sulfate. Evaporation of the solvent gave the title compound (11.87 g, 83% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.36 (m, 5H), 5.14 (s, 2H), 3.46 (t, J=6.4 Hz, 2H), 2.56 (t, J=7.2 Hz, 2H), 2.20 (quin, J=6.6 Hz, 2H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5c6f65f49c9e4a24b83927e02ad514b4
Source dataset
uspto-grants-2009_09
Patent number
US07595313B2

Reaction notes

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