Water → HCID 58045913, compound

HRID 657947Notes

Reaction equation

HRID 657947 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9]([C:11]([OH:14])([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(=O)([O-])O.[Na+]>C1COCC1>[Br:18][CH2:16][C:15]([C:7]1[CH:8]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:17]

Participants

6

Reactant 4

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

Product 1

HCID 58045913HCID 58045913, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[3-tert-Butyl-5-(1-hydroxy-1-methylethyl)phenyl]ethanone (O2.100; 50 mg) was initially charged in THF (5 ml) while stirring at RT, and admixed with phenyltrimethylammonium tribromide (80 mg). After stirring at RT for 3 h, the mixture was left to stand overnight and 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 (10 g cartridge, n-heptane/EA gradient). 42 mg of the title compound were obtained. LC-MS rt: 1.10 min [M+H—H2O]+: 295.1 (met. b)

Workup

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

Sources & evidence

ORD record
ord-c61568f52dcf450d9bdcc1611eb1f364
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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