3,5-Dimethylphenol → 4-Chloro-1-(3,5-dimethylphenoxy)-2-butanol

HRID 64689

Reaction equation

HRID 64689 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Cl:10][CH:11](O)[CH2:12][CH2:13][CH2:14]Cl.[OH-:17].[Na+]>>[Cl:10][CH2:11][CH2:12][CH:13]([OH:17])[CH2:14][O:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 3

HCID 79483,5-DimethylphenolHCID 14798Sodium HydroxideHCID 193475421,4-Dichlorobutanol

Product 1

HCID 131203444-Chloro-1-(3,5-dimethylphenoxy)-2-butanol

Conditions

Temperature
65 °C

Procedure

To a mixture of 245 g. (2 moles) of 3,5-dimethylphenol and 2 liters of 2N sodium hydroxide was added 2.5 moles of 1,4-dichlorobutanol with stirring at 65° C. overnight. The solid precipitate which separated on cooling was filtered and washed with water to neutrality. Recrystallization with isopropyl ether yielded 375 g. of white crystalline solid which melted at 74°-76° C.

Workup

  1. additionTo a mixture of 245 g
  2. customThe solid precipitate which separated
  3. temperatureon cooling
  4. filtrationwas filtered
  5. washwashed with water to neutrality
  6. customRecrystallization with isopropyl ether
  7. customyielded 375 g

Sources & evidence

ORD record
ord-ac41ec0c18c44ca8a3fe37648a717c89
Source dataset
uspto-grants-1986_09
Patent number
US04609735

Linked notes

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