Hydrochloric Acid → 6-Methoxy-1-methyl-1-trifluoromethylisochroman

HRID 1978899Notes

Reaction equation

HRID 1978899 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[CH2:14][CH2:15][O:16]C1CCCCO1)(O)[CH3:4].Cl>O>[CH3:13][O:12][C:9]1[CH:8]=[C:7]2[C:6](=[CH:11][CH:10]=1)[C:3]([CH3:4])([C:2]([F:1])([F:23])[F:24])[O:16][CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21202090HCID 21202090, compound

Product 1

HCID 102205196-Methoxy-1-methyl-1-trifluoromethylisochromanYield 138.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1,1,1-Trifluoro-2-(4-methoxy-2-(2-(tetrahydropyran-2-yloxy)ethyl)phenyl)propan-2-ol (470 mg, 1.35 mmol) and conc. hydrochloric acid (4 ml) was stirred at 120° C. for 3 hr. After cooling, the reaction mixture was diluted with water, and the aqueous layer was extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, and concentrated to give the title compound as a brown oil (460 mg). This was used without further purification.

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c2342268f838460fb3c3f5fb226afba5
Source dataset
uspto-grants-2001_05
Patent number
US06239147B1

Reaction notes

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