Benzyl Bromide → 1-Decanol, 10-(phenylmethoxy)-

HRID 2204036Notes

Reaction equation

HRID 2204036 reaction equation
[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 371531,10-Decanediol

Product 1

HCID 110108641-Decanol, 10-(phenylmethoxy)-Yield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of decane-1,10-diol (3 g, 17.21 mmol), benzyl bromide (2.25 ml, 18.94 mmol) and Ag2O (5.98 g, 25.82 mmol) in dry DCM (50 ml) were added, the reaction mixture was refluxed overnight, then the Ag2O was filtered off. The crude product was purified by silica gel column (10% EtOAc in Hexane) to afford 10-(benzyloxy)decan-1-ol as a gummy colorless liquid (2.96 g, 65%).

Workup

  1. additionwere added
  2. temperaturethe reaction mixture was refluxed overnight
  3. filtrationthe Ag2O was filtered off
  4. customThe crude product was purified by silica gel column (10% EtOAc in Hexane)

Sources & evidence

ORD record
ord-5586b571d25648b39c071a1aa85e2479
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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