Dimethylformamide → 2,2-Dimethyl-3-(4-methoxyphenylmethoxy)propanol

HRID 1284845Notes

Reaction equation

HRID 1284845 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[CH:5]([OH:7])O.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.CN(C=[O:24])C>>[CH3:3][C:4]([CH3:9])([CH2:5][O:7][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=1)[CH2:8][OH:24]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 52421202,2-Dimethylpropandiol

Product 1

HCID 109661562,2-Dimethyl-3-(4-methoxyphenylmethoxy)propanol

Procedure

A mixture of 7.7 g (0.32 mole) of sodium hydride and 80 ml of DMF was stirred under an atmosphere of N2 and cooled with an ice-water bath. A solution of 33 g (0.32 mole) of 2,2-dimethylpropandiol in 100 ml of DMF was added dropwise. Stirring was continued until the gas evolution stopped, then a solution of 50 g (0.32 mole) 4-methoxybenzyl chloride was added. The reaction mixture was stirred at room temperature overnight. The resulting solution was poured into an ice-water mixture and the aqueous solution was extracted with ethyl ether three times. The ether solution was washed with H2O, saturated brine, and then dried over MgSO4.

Workup

  1. temperaturecooled with an ice-water bath
  2. stirringStirring
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. extractionthe aqueous solution was extracted with ethyl ether three times
  5. washThe ether solution was washed with H2O, saturated brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-7ba1c74f94094d3ba26f8e9dcd7187da
Source dataset
uspto-grants-1986_01
Patent number
US04564476

Reaction notes

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