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

HRID 1382497Notes

Reaction equation

HRID 1382497 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-82dc045f818645d999e6df1ac0c7379a
Source dataset
uspto-grants-1989_02
Patent number
US04806642

Reaction notes

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