Hydrochloric Acid → 2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-1-phenylethan-1-one

HRID 548195Notes

Reaction equation

HRID 548195 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][O:7][CH2:8][C:9]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)OCC[O:10]1.Cl>C1COCC1>[F:1][C:2]([F:27])([F:28])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:22]=1)[CH2:6][O:7][CH2:8][C:9]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866240352-(3,5-Bis(trifluoromethyl)benzyloxymethyl)-2-phenyl-[1,3]dioxolane

Product 1

HCID 229606442-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-1-phenylethan-1-oneYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3,5-Bis(trifluoromethyl)benzyloxymethyl)-2-phenyl-[1,3]dioxolane (50.72 g, 140 mmol) was dissolved in THF (300 mL), 60 mol/L hydrochloric acid (50 mL) was added thereto and the mixture was heated to reflux for 20 hours. After the solvent was evaporated in vacuo, water was added to the residue followed by extracting with chloroform. The organic layers were combined, washed with water and a saturated saline solution and dried over anhydrous sodium sulfate and the solvent was evaporated in vacuo to give 2-(3,5-bis(trifluoromethyl)-benzyloxy)-1-phenylethanone (48.90 g, 96%) as an oily product. 1H-NMR (DMSO-d6) δ: 4.82 (s, 2H), 5.07 (s, 2H), 7.53-7.57 (m, 2H), 7.66-7.69 (m, 1H), 7.94-7.96 (m, 2H), 8.03 (s, 1H), 8.11 (s, 2H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 hours
  3. customAfter the solvent was evaporated in vacuo, water
  4. additionwas added to the residue
  5. extractionby extracting with chloroform
  6. washwashed with water
  7. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-708e511c7f184bc196a87d5f6b5dbaac
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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