Phenol → HCID 67333442, compound

HRID 1669642Notes

Reaction equation

HRID 1669642 reaction equation
[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][C:6]([C:15]2[CH:16]=[CH:17][C:12]([OH:18])=[CH:13][CH:14]=2)([C:15]2[CH:16]=[CH:17][C:12]([OH:18])=[CH:13][CH:14]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 2

HCID 996PhenolHCID 27774914-(Trifluoromethyl)cyclohexanone

Product 1

HCID 67333442HCID 67333442, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-(trifluoromethyl)cyclohexanone (1.13 g, 6.8 mmol) and phenol (2.01 g, 21.4 mmol) in 3 mL of concentrated HCl (aq) was stirred at 40° C. for 18 h. The reaction mixture was diluted with EtOAc and saturated aqueous NaHCO3 was slowly added. The organic layer was collected and the aqueous layer was extracted twice with EtOAc. The combined organic layers were concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with a gradient of 0% to 40% EtOAc/hexanes over 10 column volumes, then 40% to 100% EtOAc/hexanes over 5 column volumes, affording the title compound as a white solid.

Workup

  1. additionwas slowly added
  2. customThe organic layer was collected
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. concentrationThe combined organic layers were concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel eluting with a gradient of 0% to 40% EtOAc/hexanes over 10 column volumes

Sources & evidence

ORD record
ord-66dcd8f751764dc8aef01be8a59c9e70
Source dataset
uspto-grants-2011_08
Patent number
US07989472B2

Reaction notes

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