Hydrochloric Acid → [4-(1-Hydroxy-2,2-dimethylpropyl)phenyl](phenyl)methanone

HRID 2072451Notes

Reaction equation

HRID 2072451 reaction equation
[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([OH:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:14][CH:13]=3)OCC[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(O)(=O)C>[C:7]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]([OH:23])[C:19]([CH3:21])([CH3:20])[CH3:22])=[CH:16][CH:17]=1)(=[O:8])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21409408HCID 21409408, compound

Product 1

HCID 21409397[4-(1-Hydroxy-2,2-dimethylpropyl)phenyl](phenyl)methanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

14.2 gr. of the above 2-phenyl-2-(4-[1-hydroxy-2,2-dimethylpropyl]-phenyl)-1,3-dioxolane is dissolved in 500 milliliters 25% acetic acid and 5 milliliters of concentrated hydrochloric acid are added. The solution is heated on a water bath at about 60° C. for two hours. The mixture is then treated with 300 ml. of saturated sodium chloride and extracted three times with ether. The combined ether layers are washed with saturated sodium chloride solution, 2N sodium hydroxide and then dried over anhydrous magnesium sulfate and filtered. The solvent is removed and the solid recrystallized from ether-petroleum ether to give 1-(p-benzoylphenyl)-2,2-dimethylpropanol (m.p. 103°-105° C.).

Workup

  1. additionThe mixture is then treated with 300 ml
  2. extractionof saturated sodium chloride and extracted three times with ether
  3. washThe combined ether layers are washed with saturated sodium chloride solution, 2N sodium hydroxide
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent is removed
  7. customthe solid recrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-244808bf944d4e28b29914acd8f0aa2c
Source dataset
uspto-grants-1977_09
Patent number
US04051261

Reaction notes

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