Water → 2,2-Dimethyl-3-(3-phenyl-2-propenoxy)propanol

HRID 1284847Notes

Reaction equation

HRID 1284847 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[CH:5]([OH:7])O.[C:10]1([CH:16]=[CH:17][CH2:18]Cl)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH2:20]>CN(C=O)C>[CH3:3][C:4]([CH3:9])([CH2:5][O:7][CH2:18][CH:17]=[CH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:8][OH:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 52421202,2-Dimethylpropandiol

Product 1

HCID 539836772,2-Dimethyl-3-(3-phenyl-2-propenoxy)propanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In a dry three-neck flask under an atmosphere of N2 was placed 14.4 g (0.6 mole) of NaH and 100 ml of DMF. The mixture was stirred and a solution of 52.1 g (0.5 mole) of 2,2-dimethylpropandiol in 75 ml of DMF was added dropwise. Stirring was continued until the gas evolution ceased, then a solution of 91.57 g (0.6 mole) of 3-phenyl-2-propenyl chloride in 50 ml of DMF was added. The reaction mixture was stirred at room temperature for two days, then poured into 500 ml of ice and water. The aqueous solution was extracted with three 300 ml portions of ethyl ether. The organic layers were combined and washed with H2O, saturated NaCl solution, and then dried over MgSO4. The solvent was removed on a rotary evaporator to give a brick red liquid. Kugelrohr distillation gave the title compound, bp 100°-110°/0.025-0.005 mm Hg. The product was a mixture of cis and trans isomers.

Workup

  1. customIn a dry three-neck flask under an atmosphere of N2 was placed
  2. stirringStirring
  3. stirringThe reaction mixture was stirred at room temperature for two days
  4. extractionThe aqueous solution was extracted with three 300 ml portions of ethyl ether
  5. washwashed with H2O, saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed on a rotary evaporator
  8. customto give a brick red liquid
  9. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-7012f567f28343da985e640a0a5b5498
Source dataset
uspto-grants-1986_01
Patent number
US04564476

Reaction notes

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