Dimethylformamide → 4-Benzyloxy-1-butanol

HRID 1838893Notes

Reaction equation

HRID 1838893 reaction equation
[H-].[Na+].CN(C=O)C.[CH2:8]([OH:13])[CH2:9][CH2:10][CH2:11][OH:12].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH2:14]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 7498Benzyl BromideHCID 80641,4-ButanediolHCID 24758Sodium hydride

Product 1

HCID 5622124-Benzyloxy-1-butanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-20 °C

Procedure

42 a of sodium hydride (60% strength) are introduced in portions into 900 ml of abs. DMF at room temperature. 88.6 ml of 1,4-butanediol in 450 ml of abs. DMF are added dropwise to the suspension cooled to −20° C. such that the internal temperature does not exceed −15° C. After addition is complete, a solution of 121 ml of benzyl bromide in 870 ml of abs. DMF is rapidly added dropwise and the reaction mixture is then stirred at room temperature for 30 minutes. The reaction is ended by careful addition of 315 ml of water. For work-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 over magnesium sulphate and concentrated in vacuo. Chromatography on silica gel using a hexane-ethyl acetate gradient yields 105 g of 4-benzyloxybutan-1-ol as an oil.

Workup

  1. customat room temperature
  2. customdoes not exceed −15° C
  3. additionAfter addition
  4. extractionextracted 3 times with 1 l of ether in each case
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad94809c2f49424787a0407ff105a930
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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