Methanol → HCID 59200951, compound

HRID 1919754Notes

Reaction equation

HRID 1919754 reaction equation
N1C=CC=CC=1.[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:23])([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[CH2:24][CH2:25][CH3:26].[C:27](OC(=O)C)(=[O:29])[CH3:28].CO>ClCCl>[C:27]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:23])([C:15]([F:16])([F:17])[F:18])[C:19]([F:20])([F:21])[F:22])=[CH:10][C:9]=1[CH2:24][CH2:25][CH3:26])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 59201025HCID 59201025, compound

Product 1

HCID 59200951HCID 59200951, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (14.7 mL) was added to 2-(4-hydroxy-3-propylphenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (13.76 g, 45.5 mmol) in dichloromethane (200 mL) at room temperature, and then acetic anhydride (17.3 mL) was added. After stirring overnight, methanol (300 mL) was added. After stirring at room temperature for one hour, the reaction solution was concentrated under reduced pressure. Water was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 13.67 g of the title compound (yield: 87%) as a red brown oil.

Workup

  1. stirringAfter stirring at room temperature for one hour
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionWater was added to the resulting residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-57c5cd2aa0d6413191366e983e3d907e
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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