Ethanol → HCID 14032768, compound

HRID 986683Notes

Reaction equation

HRID 986683 reaction equation
C(C1[CH:8]=[CH:7][C:6]([C:9](=[O:25])[C:10]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=2)=[CH:5][CH:4]=1)#N.[OH-:26].[Na+].[CH2:28]([OH:30])[CH3:29]>>[C:28]([C:29]1[CH:8]=[CH:7][C:6]([C:9](=[O:25])[C:10]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=2)=[CH:5][CH:4]=1)([OH:26])=[O:30]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 140327674-[3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzoyl]benzonitrile

Product 1

HCID 14032768HCID 14032768, compound

Procedure

A mixture of 3.35 g (0.010 mole) of 4'-cyano-3,5-di(tertiary-butyl)-4-hydroxybenzophenone, 25 ml of 20% aqueous sodium hydroxide solution and 25 ml of ethanol was heated at its reflux temperature for about 16 hours. The solution was extracted and washed twice with dichloromethane. The aqueous portion was poured into cold dilute hydrochloric acid and a white solid precipitated. The solid was collected by filtration and was washed with water. The solid was recrystallized from about 50 ml of ethanol with treatment with decolorizing charcoal to provide white solid 4'-carboxy-3,5-di(tertiary-butyl)-4-hydroxybenzophenone, m.p. 248.5°250.5° C. Analysis: Calculated for C22H26O4 : %C, 74.6; %H, 7.4; Found: %C, 74.7; %H, 7.5.

Workup

  1. temperaturewas heated at its
  2. temperaturereflux temperature for about 16 hours
  3. extractionThe solution was extracted
  4. washwashed twice with dichloromethane
  5. additionThe aqueous portion was poured into cold dilute hydrochloric acid
  6. customa white solid precipitated
  7. filtrationThe solid was collected by filtration
  8. washwas washed with water
  9. customThe solid was recrystallized from about 50 ml of ethanol with treatment with decolorizing charcoal

Sources & evidence

ORD record
ord-acdc2476d8e8485989f5367ee5da304e
Source dataset
uspto-grants-1987_12
Patent number
US04714776

Reaction notes

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