Benzyl Alcohol → Benzyl 4-bromobutanoate

HRID 486244Notes

Reaction equation

HRID 486244 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].CN1CCOCC1.[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[CH2:15]([O:22][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Br:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 79724-MethylmorpholineHCID 702254-Bromobutyryl chloride

Product 1

HCID 3832489Benzyl 4-bromobutanoateYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

In the first step, 4-bromobutyryl chloride (13.8 g, 75 mmole) was placed in a 100 ml round bottom flask. The flask was cooled to -20° C. using a dry ice/carbon tetrachloride bath. Ethyl acetate (50 ml) containing N-methylmorpholine (7.58 g, 75 mmole, 8.2 ml) was added carefully. Using an addition funnel, benzyl alcohol (6.97 g, 6.67 ml, 6.64 mmoles) was added dropwise. After the addition the bath was removed and the mixture was stirred for 2 hours. The product was transferred to a separatory funnel using ethyl acetate (50 ml), washed once with sodium bicarbonate (10%), then twice with water, and dried with anhydrous sodium sulfate. Evaporation of solvents gave benzyl-4-bromo-butyrate as an oil (yield=91%).

Workup

  1. additionwas added carefully
  2. additionAfter the addition the bath
  3. customwas removed
  4. customThe product was transferred to a separatory funnel
  5. washwashed once with sodium bicarbonate (10%)
  6. dry with materialtwice with water, and dried with anhydrous sodium sulfate
  7. customEvaporation of solvents

Sources & evidence

ORD record
ord-e10ec403d9ef40d181c4658a2a1b1af4
Source dataset
uspto-grants-1994_03
Patent number
US05290936

Reaction notes

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