Water → HCID 58045825, compound

HRID 657948Notes

Reaction equation

HRID 657948 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9]([C:11](O)([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-:18].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.O.[C:52](=[O:55])([O-])O.[Na+]>C1COCC1.CO>[Br:18][CH2:16][C:15]([C:7]1[CH:8]=[C:9]([C:11]([O:55][CH3:52])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58045827HCID 58045827, compound

Product 1

HCID 58045825HCID 58045825, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[3-tert-Butyl-5-(1-hydroxy-1-methylethyl)phenyl]ethanone (O2.100; 500 mg) was initially charged in a mixture of THF and methanol (3.5/3.5 ml) while stirring at RT, and admixed with phenyltrimethylammonium tribromide (800 mg). After stirring at RT for 7 h, the mixture was admixed with water and saturated sodium hydrogencarbonate solution. Then it was extracted three times with EA, and the combined EA phases were dried over sodium sulfate, filtered and concentrated. The residue was purified using silica gel (70 g cartridge, n-heptane/EA gradient). 454 mg of the title compound were obtained. LC-MS rt: 1.23 min [M+H—HOMe]+: 295.1 (met. b)

Workup

  1. stirringAfter stirring at RT for 7 h
  2. extractionThen it was extracted three times with EA
  3. dry with materialthe combined EA phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-ddae02098f1144dfa676b6ffb738f991
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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