Citric Acid → HCID 58136875, compound

HRID 657941Notes

Reaction equation

HRID 657941 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:21](=[O:23])[CH3:22])[CH:8]=[C:9]([O:11][CH2:12][CH2:13][O:14]C2CCCCO2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-:24].[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:24][CH2:22][C:21]([C:7]1[CH:8]=[C:9]([O:11][CH2:12][CH2:13][OH:14])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)=[O:23]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58136945HCID 58136945, compound

Product 1

HCID 58136875HCID 58136875, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-{3-tert-Butyl-5-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}ethanone (O2.061; 3.9 g) was dissolved in methanol/THF (60 ml/60 ml) and admixed while stirring with phenyltrimethylammonium tribromide (5.03 g). After stirring at RT for 3 h, the reaction mixture was added to 20% citric acid and stirred for 1 h. After adding EA, the EA phase was removed, dried and concentrated. The residue was purified using silica gel (80 g cartridge, n-heptane/EA gradient of 0-50% within 60 min). 2.56 g of the title compound were obtained.

Workup

  1. stirringstirred for 1 h
  2. customthe EA phase was removed
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customsilica gel (80 g cartridge, n-heptane/EA gradient of 0-50% within 60 min)

Sources & evidence

ORD record
ord-df2ddee6541b4161a4335389909ae9a7
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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