4-Chlorophenol → 1-(4-Chlorophenoxy)-3,3-dimethylbutan-2-ol

HRID 1759270Notes

Reaction equation

HRID 1759270 reaction equation
[C:1]([CH:5]1[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[OH-].[Na+]>O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:7][CH:5]([OH:6])[C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 14798Sodium HydroxideHCID 921742-tert-Butyloxirane

Product 1

HCID 127742501-(4-Chlorophenoxy)-3,3-dimethylbutan-2-olYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

5 g (0.05 mole) of tert.-butyloxirane were added to 12.8 g (0.1 mole) of 4-chlorophenol and 4 g of sodium hydroxide in 20 ml of water. The reaction mixture was stirred at 60° C. for 24 hours and then diluted with about 100 ml of water. It was extracted three times with 50 ml of methylene chloride each time. The combined organic phases were washed with dilute aqueous sodium hydroxide solution for the purpose of removing unreacted phenol, and were dried over sodium sulpnate and concentrated. The residue was distilled in vacuo. 5.9 g (52% of theory) of 1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-ol of boiling point 105° C./0.5 mm Hg were obtained.

Workup

  1. extractionIt was extracted three times with 50 ml of methylene chloride each time
  2. washThe combined organic phases were washed with dilute aqueous sodium hydroxide solution for the purpose
  3. customof removing unreacted phenol
  4. dry with materialwere dried over sodium sulpnate
  5. concentrationconcentrated
  6. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-eb363460c151470bba9b9a37ffc48594
Source dataset
uspto-grants-1982_07
Patent number
US04339612

Reaction notes

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