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

HRID 1382377Notes

Reaction equation

HRID 1382377 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-butanol

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 500 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. temperature, cooled
  3. extractionextracted with 300 ml
  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
  9. customyielded 180 g

Sources & evidence

ORD record
ord-cfeb7472fccd484f89a8a1da1d0d3a59
Source dataset
uspto-grants-1989_02
Patent number
US04806555

Reaction notes

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