4-Hydroxybiphenyl → 4-Chloro-(4-biphenylyloxy)-2-butanol

HRID 1639056Notes

Reaction equation

HRID 1639056 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl[CH2:17][CH:18]([OH:22])[CH2:19][CH2:20][Cl:21]>O>[Cl:21][CH2:20][CH2:19][CH:18]([OH:22])[CH2:17][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 14798Sodium HydroxideHCID 170211,4-Dichloro-2-butanol

Product 1

HCID 131203474-Chloro-(4-biphenylyloxy)-2-butanolYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1 mole (158 g) of 4-phenylphenol, 100 g of sodium hydroxide and 400 ml of water was added 1 mole (143.02 g) of 1,4-dichloro-2-butanol with stirring at 40° C. The resulting mixture was heated at 68° C. in a steam bath for 6 hr, cooled and extracted with 300 ml of chloroform. The chloroform extract was washed with water to neutrality, dried over sodium sulfate and concentrated to dryness. The solid residue was recrystallized with isopropanol and yielded 180 g of a white crystalline solid which melted at 123°-124° C.

Workup

  1. temperatureThe resulting mixture was heated at 68° C. in a steam bath for 6 hr
  2. temperaturecooled
  3. extractionextracted with 300 ml of chloroform
  4. extractionThe chloroform extract
  5. washwas washed with water to neutrality
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe solid residue was recrystallized with isopropanol

Sources & evidence

ORD record
ord-b8802f02b3dd41f99125100ea6c6622c
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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