Water → 5-(Benzyloxy)pentan-1-ol

HRID 1837216Notes

Reaction equation

HRID 1837216 reaction equation
[H-].[Na+].[CH2:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CN(C=O)C>[CH2:10]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 7498Benzyl BromideHCID 81051,5-PentanediolHCID 24758Sodium hydride

Product 1

HCID 2211945-(Benzyloxy)pentan-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
-20 °C

Procedure

31.5 g of sodium hydride (60%) is introduced at room temperature in portions in 900 ml of absolute DMF. 104.8 ml of 1,5-pentanediol in 450 ml of absolute DMF is added in drops to the suspension that is cooled to −20° C. in such a way that the internal temperature does not exceed −15° C. After the addition has been completed, a solution of 121 ml of benzyl bromide in 870 ml of absolute DMF is quickly added in drops, and then the reaction mixture is stirred for 30 minutes at room temperature. The reaction is completed by careful addition of 315 ml of water. For working-up, the reaction mixture is stirred into 1.5 l of water and extracted 3 times with 1 l of ether in each case. The ethereal phases are combined, washed with water, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Chromatography on silica gel with a hexane-ethyl acetate gradient yields 85 g of 5-benzyloxy-pentan-1-ol as an oil.

Workup

  1. customdoes not exceed −15° C
  2. additionAfter the addition
  3. extractionextracted 3 times with 1 l of ether in each case
  4. washwashed with water
  5. customdried on magnesium sulfate
  6. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-5823b02019d64bbf93d9f6bd06fb2d7b
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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