Benzyl Alcohol → Benzyl 4-bromobutanoate

HRID 989931Notes

Reaction equation

HRID 989931 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8](O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>S(Cl)(Cl)=O>[CH2:8]([O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][Br:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 758094-Bromobutyric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 3832489Benzyl 4-bromobutanoate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
-50 °C

Procedure

4-bromobutyric acid (10.6 g, 60 mmole) was dissolved in thionyl chloride (20 mml), and the reaction was kept for 4 hr. The solution was evaporated and coevaporated with toluene several times. The residue was redissolved in dichloromethane (120 ml), and then benzyl alcohol (4.14 ml, 40 mmole) was added. The solution was cooled down to −50° C. and triethylamine (10 ml, 72 mmole) was added. The reaction mixture was slowly warmed to room temperature. After 3 hr, the reaction mixture was poured into sodium bicarbonate aqueous solution and the organic phase was washed with water and dried, giving the titled product, 6.8 g.

Workup

  1. customThe solution was evaporated
  2. dissolutionThe residue was redissolved in dichloromethane (120 ml)
  3. temperatureThe reaction mixture was slowly warmed to room temperature
  4. waitAfter 3 hr
  5. washthe organic phase was washed with water
  6. customdried

Sources & evidence

ORD record
ord-6980ea5fd2bc408c8a244732f78981ec
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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