Resorcinol → 3,5-Di-tert-butyl-2',4,4'-trihydroxybenzophenone

HRID 327909Notes

Reaction equation

HRID 327909 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](Cl)=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:19]1([CH:26]=[CH:25][CH:24]=[C:22]([OH:23])[CH:21]=1)[OH:20].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([C:24]1[CH:25]=[CH:26][C:19]([OH:20])=[CH:21][C:22]=1[OH:23])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 197339413,5-Di-tert-butyl-2',4,4'-trihydroxybenzophenoneYield 90.8%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

107.5 g of 3,5-di-tert-butyl-4-hydroxybenzoyl chloride and 48.4 g of resorcinol are suspended in 400 ml of nitrobenzene and warmed to 50° C. The brown solution is cooled to 0° C. 58.7 g of aluminium chloride are added in portions over the course of 45 minutes with vigorous stirring. The reaction mixture is slowly warmed to 20° C. over the course of 18 hours. The mixture is subsequently stirred at 50° C. for a further 4 hours, then cooled to room temperature and poured into 500 ml of hydrochloric acid/ice. The thick yellow suspension is extracted with ether, the ether phase is extracted with 500 ml of sodium hydroxide (15%), and the basic solution is washed three times with 250 ml of ether in each case, acidified to a pH of 1-2 using 15% hydrochloric acid and extracted with ether. The ether extracts are combined, dried and evaporated under reduced pressure, giving 124.4 g of 3,5-di-tert-butyl-2',4,4'-trihydroxybenzophenone, which, after recrystallisation from methanol, has a melting point of 192°-193° C.

Workup

  1. temperatureThe brown solution is cooled to 0° C
  2. temperatureThe reaction mixture is slowly warmed to 20° C. over the course of 18 hours
  3. temperaturecooled to room temperature
  4. extractionThe thick yellow suspension is extracted with ether
  5. extractionthe ether phase is extracted with 500 ml of sodium hydroxide (15%)
  6. washthe basic solution is washed three times with 250 ml of ether in each case
  7. extractionextracted with ether
  8. customdried
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9028e888f9b44ad4a029650a415007d4
Source dataset
uspto-grants-1993_12
Patent number
US05274170

Reaction notes

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