Water → 3-(2-Methoxy-phenoxy)-3-phenyl-propylene

HRID 903963Notes

Reaction equation

HRID 903963 reaction equation
[Na].[C:2]1([O:9][CH3:10])[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:11]1([CH:17](Cl)[CH:18]=[CH2:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CN(C)C=O>[CH3:10][O:9][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 962WaterHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 70053666HCID 70053666, compound

Product 1

HCID 234583923-(2-Methoxy-phenoxy)-3-phenyl-propyleneYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5 g of guaiacol sodium salt in 60 ml of dimethylformamide, 1-phenylallyl-chloride (5.22 g) (J.C.S. 1959, p. 2720) was added under a nitrogen atmosphere. The whole was stirred for 4 hours at room temperature and for two hours at 50° C., poured into water and extracted with ethyl ether. After standard working up, followed by chromatographic separation, 3-(2-methoxy-phenoxy)-3-phenyl-propylene (8.1 g; 98%) was obtained.

Workup

  1. extractionextracted with ethyl ether
  2. customfollowed by chromatographic separation

Sources & evidence

ORD record
ord-25e5f80f89de4d9899f4f41e4d5e1337
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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