1-Butanol → 1-(Benzyloxy)-3-butoxypropan-2-ol

HRID 2372327Notes

Reaction equation

HRID 2372327 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:8]([O:15][CH2:16][CH:17]1[O:19][CH2:18]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C.O>[CH2:1]([O:5][CH2:18][CH:17]([OH:19])[CH2:16][O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 2631-ButanolHCID 24758Sodium hydride2×HCID 94247Benzyl glycidyl ether

Product 1

HCID 30211351-(Benzyloxy)-3-butoxypropan-2-olYield 48.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

n-Butanol (2.5 ml, 27 mmol) is added to a suspension of sodium hydride (50% in mineral oil; 1.3 g, 27 mmol) in DMF (5 ml) and the mixture is then heated to 80° C. for 1.0 hours when all the sodium hydride is consumed. A solution of 2,3-epoxypropyl benzyl ether (benzyl glycidylether*) (4.52 g, 27 mmol) in DMF (5 ml) is added slowly to the n-butoxide solution. The mixture is then heated to 80° C. for 16 hours, diluted with water and extracted with ether. The ether layer is dried and concentrated to give an oil which is distilled to provide the desired product (3.1 g), bp 125°-130°/0.8-0.5 mm.

Workup

  1. customis consumed
  2. extractionextracted with ether
  3. dry with materialThe ether layer is dried
  4. concentrationconcentrated
  5. customto give an oil which
  6. distillationis distilled

Sources & evidence

ORD record
ord-4ba11f73662e4aad957321c10cb28ec1
Source dataset
uspto-grants-1992_03
Patent number
US05098906

Reaction notes

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