Citric Acid → HCID 58045794, compound

HRID 1524533Notes

Reaction equation

HRID 1524533 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:22](=[O:24])[CH3:23])[CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15]C2CCCCO2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-:25].[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.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CC(=O)OCC>CO.C1COCC1>[Br:25][CH2:23][C:22]([C:7]1[CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)=[O:24]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58136802HCID 58136802, compound

Product 1

HCID 58045794HCID 58045794, compoundYield 116.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-{3-tert-Butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]phenyl}ethanone (O2.059; 3.4 g) was dissolved in methanol/THF (50/50 ml) and admixed while stirring with phenyltrimethylammonium tribromide (4.21 g). After stirring at RT for 3 h, 20% citric acid solution was added and the mixture was stirred for 1 h. Then EA was added and the EA phase was removed. The EA phase was dried over magnesium sulfate and concentrated by rotary evaporation. The residue was purified by means of silica gel (80 g cartridge, n-heptane/EA gradient of 0-50% within 60 min). 2.49 g of the title compound were obtained.

Workup

  1. stirringthe mixture was stirred for 1 h
  2. customthe EA phase was removed
  3. dry with materialThe EA phase was dried over magnesium sulfate
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by means of silica gel (80 g cartridge, n-heptane/EA gradient of 0-50% within 60 min)

Sources & evidence

ORD record
ord-3eea77fada26441e91cf87f554feb28f
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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