Dimethyl Sulfate → HCID 20513479, compound

HRID 1164067Notes

Reaction equation

HRID 1164067 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:6][C:3]=1[CH:4]=[O:5].S(OC)(O[CH3:22])(=O)=O>[OH-].[K+]>[CH3:22][O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 20513447HCID 20513447, compound

Product 1

HCID 20513479HCID 20513479, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

An aqueous solution (30 ml) of potassium hydroxide (8.2 g) was added portionwise to a mixture of 2-hydroxy-5-(2-chlorophenoxy)benzaldehyde (10.4 g) and dimethyl sulfate (10.5 g) with stirring at room temperature, and the mixture was stirred at 70° C. for an hour. After cooling, the reaction mixture was extracted with diethyl ether, and the extract was washed with water, dried and evaporated. The residue was crystallized from methanol to give 2-methoxy-5-(2-chlorophenoxy)benzaldehyde (8 g). mp 65°-66° C.

Workup

  1. stirringthe mixture was stirred at 70° C. for an hour
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with diethyl ether
  4. washthe extract was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-5dbe81ccbacc4b8a902cc1867ca96de9
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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