Dimethylformamide → 1-Propanol, 2,2-dimethyl-3-(phenylmethoxy)-

HRID 1284843Notes

Reaction equation

HRID 1284843 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[CH:5]([OH:7])O.[H][H].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(C=[O:24])C>>[CH3:3][C:4]([CH3:9])([CH2:5][O:7][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][OH:24]

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 52421202,2-DimethylpropandiolHCID 178418361HCID 178418361, compound

Product 1

HCID 111271431-Propanol, 2,2-dimethyl-3-(phenylmethoxy)-

Procedure

A mixture of 29.0 g (1.2 moles) of sodium hydride and 200 ml of dry DMF was stirred under an atmosphere of N2 and cooled with an ice-water bath. A solution of 125 g (1.20 moles) of 2,2-dimethylpropandiol in 100 ml of dry DMF was added with stirring. After the hydrogen gas evolution ceased, 139 ml (1.20 moles) of benzyl chloride was added and the reaction mixture was stirred at room temperature overnight. The resulting reaction solution was poured into ice-water (300 ml) and the aqueous solution was extracted with ethyl ether three times. The organic solutions were combined and washed with NaCl solution and then dried over Na2SO4. The residue, after removal of solvent, was distilled through a vigreux column to obtain the title compound, bp. 85°-87°/0.02 mmHg, as a colorless liquid.

Workup

  1. temperaturecooled with an ice-water bath
  2. stirringwith stirring
  3. stirringthe reaction mixture was stirred at room temperature overnight
  4. customThe resulting reaction solution
  5. extractionthe aqueous solution was extracted with ethyl ether three times
  6. washwashed with NaCl solution
  7. dry with materialdried over Na2SO4
  8. customThe residue, after removal of solvent
  9. distillationwas distilled through a vigreux column

Sources & evidence

ORD record
ord-7cc07fa680264c89bbec8d05ce2d7f02
Source dataset
uspto-grants-1986_01
Patent number
US04564476

Reaction notes

Loading…