Water → 4(4-Chloro-3,5-dimethyl-phenoxy)-2,6-dimethylanisole

HRID 1074516Notes

Reaction equation

HRID 1074516 reaction equation
[OH-:1].[Na+].O.Br[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[C:7]([CH3:14])[CH:6]=1.[CH2:15]([Cl:17])Cl>>[Cl:17][C:15]1[C:9]([CH3:8])=[CH:10][C:5]([O:1][C:5]2[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[C:7]([CH3:14])[CH:6]=2)=[CH:6][C:7]=1[CH3:14]

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 2786544-Bromo-2,6-dimethylanisole

Product 1

HCID 127678104(4-Chloro-3,5-dimethyl-phenoxy)-2,6-dimethylanisole

Procedure

A mixture of 94 g of 4-chloro-3,5-dimethyl-phenol, 129 g of 4-bromo-2,6-dimethyl-anisole, 40 g of potassium hydroxide and 5 g of copper powder was slowly heated to 180°-190° C. During this operation, first the corresponding potassium phenolate formed, and the water formed separated by distillation with a small amount of 4-bromo-2,6-dimethylanisole. At about 200°-220° C., further reaction yielding phenoxy-anisole took place. After about 4 to 5 hours, the reaction was complete. The cooled substance was extracted to exhaustion with a solvent which is not miscible with water, such as methylene chloride. The filtrate of inorganic salts formed was then shaken several times with 2 N sodium hydroxide solution and water. After vaporization of methylene chloride a crude product was obtained which was still contaminated by 4-bromo-2,6-dimethyl-anisole. After distillation, 86 g of 4(4-chloro-3,5-dimethyl-phenoxy)-2,6-dimethyl-anisole were obtained, boiling point: 186° C. under a pressure of 3 mm mercury.

Workup

  1. extractionThe cooled substance was extracted to exhaustion with a solvent which
  2. customThe filtrate of inorganic salts formed
  3. distillationAfter distillation

Sources & evidence

ORD record
ord-cff8674d290f453d9095e3cc277f9a2d
Source dataset
uspto-grants-1983_07
Patent number
US04391995

Reaction notes

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