Hydrochloric Acid → 3-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclohexanone

HRID 11217Notes

Reaction equation

HRID 11217 reaction equation
C1CO[C:3]2([CH2:8][CH2:7][CH2:6][C:5]([CH2:15][O:16][CH2:17][C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:4]2)[O:2]1.Cl.C(=O)(O)[O-].[Na+].ClCCl>CC(C)=O>[F:25][C:24]([F:26])([F:27])[C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:21]=1)[CH2:17][O:16][CH2:15][C:5]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:7][CH2:8][C:3](=[O:2])[CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 219731201-(((3,3-Ethylenedioxy-1-phenylcyclohexyl)methoxy)methyl)-3,5-bis(trifluoromethyl)benzene

Product 1

HCID 219731213-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclohexanoneYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-(((3,3-ethylenedioxy-1-phenylcyclohexyl)methoxy)methyl)-3,5-bis(trifluoromethyl)benzene (990 mg, 2.09 mmol) in acetone (4 mL) at room temperature were added 1N HCl solution (3.13 mL) and the resulting mixture was stirred at reflux for 2 hr. After cooling down, saturated sodium bicarbonate and dichloromethane were added and the organic layer was separated. The aqueous layer was extracted with dichloromethane 2 times and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum to give the title compound as clear pale yellow sticky oil (830 mg, 92% yield). 1H NMR (400 MHz, CDCl3) δ 1.60 (1H, m), 1.88 (1H, m), 2.19–2.24 (2H, m), 2.29–2.32 (2H, m), 2.85 (2H, dd, J=12, 68 Hz), 3.51 (2H, dd, J=12, 56 Hz), 4.52 (2H, dd, J=16, 18 Hz), 7.22–7.25 (1H, m), 7.32 (4H, d, J=4 Hz), 7.63 (2H, s), 7.77 (1H, s). HPLC purity (retention time): 90% (2.32 min, method C). MS: 453.37 (M+Na+).

Workup

  1. temperatureat reflux for 2 hr
  2. temperatureAfter cooling down
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane 2 times
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-85e3a2687cd244519163a64ff49e61c4
Source dataset
uspto-grants-2006_08
Patent number
US07098203B2

Reaction notes

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