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Tetrahydrofuran → 4'-[3,5-Di-tert-butyl-4-hydroxyphenylpropionyloxy]-3,5-di-tert-butyl-2',4-dihydroxybenzophenone

HRID 327910
Notes
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Reaction equation

HRID 327910 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[OH:17])=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:26](N(CC)CC)C.C([C:37]1[CH:38]=[C:39]([CH2:48][CH2:49][C:50](Cl)=[O:51])[CH:40]=[C:41]([C:44]([CH3:47])([CH3:46])[CH3:45])[C:42]=1[OH:43])(C)(C)C.O1[CH2:57][CH2:56][CH2:55]C1>C1(C)C=CC=CC=1>[C:56]([CH:48]([C:39]1[CH:40]=[C:41]([C:44]([CH3:45])([CH3:46])[CH3:47])[C:42]([OH:43])=[CH:37][CH:38]=1)[CH2:49][C:50]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[C:7]2[CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]([OH:21])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)=[C:11]([OH:17])[CH:12]=1)=[O:51])([CH3:55])([CH3:57])[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 156069683-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionyl chlorideHCID 197339413,5-Di-tert-butyl-2',4,4'-trihydroxybenzophenone

Product 1

HCID 867461304'-[3,5-Di-tert-butyl-4-hydroxyphenylpropionyloxy]-3,5-di-tert-butyl-2',4-dihydroxybenzophenone

Reagents, catalysts & solvents

1
HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

12.0 g of 3,5-di-tert-butyl-2',4,4'-trihydroxybenzophenone and 3.9 g of triethylamine are dissolved in 20 ml of tetrahydrofuran and 40 ml of toluene. The orange-beige solution is cooled to 0° C. A solution of 11.2 g of 3,5-di-tert-butyl-4-hydroxyphenylpropionyl chloride in 40 ml of toluene is added dropwise at between 0° and 5° C. over the course of 1 hour with vigorous stirring, and the mixture is subsequently stirred at room temperature for 2days. The reaction mixture is poured into 700 ml of ice-water, and the phases are separated. The aqueous phase is extracted with toluene, and the toluene phases are combined, washed, dried and evaporated under reduced pressure. The beige oil is chromatographed on silica gel and recrystallised from petroleum ether (40°-60° C.)/ethyl acetate, giving 21.0 g of 4'-[3,5-di-tert-butyl-4-hydroxyphenylpropionyloxy]-3,5-di-tert-butyl-2',4-dihydroxybenzophenone of melting point 145°-147° C.

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted with toluene
  3. washwashed
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe beige oil is chromatographed on silica gel
  7. customrecrystallised from petroleum ether (40°-60° C.)/ethyl acetate

Sources & evidence

ORD record
ord-9cc666682e934a92b278a7e6a2e10daf
Source dataset
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05274170

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes