Benzyl Bromide → Tetrabenzylpentaerythritol

HRID 1162943Notes

Reaction equation

HRID 1162943 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH:11][CH2:12][C:13]([CH2:18][OH:19])([CH2:16][OH:17])[CH2:14][OH:15].[Cl-].[NH4+]>CN(C=O)C>[CH2:3]([O:11][CH2:12][C:13]([CH2:18][O:19][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH2:16][O:17][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:14][OH:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8285PentaerythritolHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 12082528TetrabenzylpentaerythritolYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (440 mg, 11.01 mmol) and benzyl bromide (1.3 mL, 11.01 mmol) were added to 20 mL of a solution of pentaerythritol (500 mg, 3.67 mmol) in DMF, and the mixture was stirred at room temperature for 14 hours. Aqueous saturated ammonium chloride was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 3-benzyloxy-2,2-bis(benzyloxymethyl)propan-1-ol (560 mg, 38%) as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-3fbdb400f3c4428d914202e1fbe3853f
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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