Benzyl Bromide → Benzyl 4-hydroxybutanoate

HRID 1648199

Reaction equation

HRID 1648199 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([O-:7])=[O:6].[Na+].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C.C(OCC)(=O)C>[OH:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 23663870Sodium Oxybate

Product 1

HCID 14443958Benzyl 4-hydroxybutanoateYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Sodium 4-hydroxybutyrate (25 g, 0.2 mol) and benzyl bromide (37 g, 0.22 mol) were dissolved in a mixed solvent of DMF (40 ml) and ethyl acetate (50 ml), and the reaction mixture was heated and refluxed for 4 hours. Then, the reaction mixture was allowed to cool to room temperature, diluted with a proper amount of ethyl acetate, washed with saturated saline solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oily product. The resulted product was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=4/1) to give 34.9 g of benzyl 4-hydroxybutyrate. Yield: 90%.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperaturerefluxed for 4 hours
  3. washwashed with saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oily product
  7. customThe resulted product was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-8589ef1ff6444beb9f10a15383b1c7f5
Source dataset
uspto-grants-1995_07
Patent number
US05436221

Linked notes

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