Benzyl Bromide → 4-Benzyloxy-1-butanol

HRID 1792364Notes

Reaction equation

HRID 1792364 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CCCCCC.C([O:20][CH2:21][CH3:22])(=O)C.C1C[O:26][CH2:25][CH2:24]1>>[C:4]1([CH2:3][O:26][CH2:25][CH2:24][CH2:22][CH2:21][OH:20])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 8058HexaneHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 5622124-Benzyloxy-1-butanolYield 16%

Procedure

To a solution of diol compound (4.51 g, 50 mmol) in dry THF (50 ml) was added 60% NaH (1.6 g, 43 mmol) at 0° C. After stirring for 2 hours, benzyl bromide (5.7 g, 33 mmol) was added dropwise and stirred for 15 hours. After the reaction was completed, ice-water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The organic solvent was removed under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=10:1) to give the title compound (936 mg, yield: 16%).

Workup

  1. stirringstirred for 15 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe organic solvent was removed under reduced pressure
  7. customto give a crude product
  8. customThis crude product thus obtained

Sources & evidence

ORD record
ord-4d36a91cb6554254afe25a8ebb482884
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

Loading…