Dimethyl Sulfate → HCID 13066664, compound

HRID 1163991Notes

Reaction equation

HRID 1163991 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH:12]=[CH2:13])[C:6]=1[OH:14].S(OC)(O[CH3:23])(=O)=O>[OH-].[K+]>[CH3:23][O:14][C:6]1[C:7]([CH2:11][CH:12]=[CH2:13])=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][C:3]1[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 20513462HCID 20513462, compound

Product 1

HCID 13066664HCID 13066664, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

An aqueous solution (100 ml) of potassium hydroxide (17.0 g) was added all at once to a mixture of 2-(2-chlorophenoxy)-6-allylphenol (22.0 g) and dimethyl sulfate (23.0 g) under cooling. The mixture was stirred at room temperature for 30 minutes and extracted with diethyl ether. The extract was washed with water 3 times, dried over magnesium sulfate and then evaporated. The oily residue was subjected to distillation under reduced pressure to give colorless oil of 2-chlorophenyl 2-methoxy-3-allylphenyl ether (22.0 g). bp 149° C./0.8 mmHg.

Workup

  1. temperatureunder cooling
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water 3 times
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. distillationThe oily residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-97f251a7986c44cab1bce40fd9b12d99
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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