3-(Trifluoromethyl)phenol → HCID 19705216, compound

HRID 727197Notes

Reaction equation

HRID 727197 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].CS(O[CH:19]1[CH2:28][CH2:27][C:22]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:21][CH2:20]1)(=O)=O>C1(C)C=CC=CC=1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH:19]1[CH2:28][CH2:27][C:22]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Product 1

HCID 19705216HCID 19705216, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 4.5 grams (0.028 mole) of 3-trifluoromethylphenol and 1.1 grams (0.028 mole) of sodium hydride (60% in mineral oil) in 100 mL of toluene is stirred at ambient temperature for about 20 minutes, and a solution of 6.6 grams (0.028 mole) of 8-methylsulfonyloxy-1,4-dioxaspiro[4.5]decane (prepared as in Step C of Example 8) in 20 mL of toluene is added dropwise. Upon complete addition, the reaction mixture is heated to reflux where it is stirred for about four hours. The reaction mixture is cooled and concentrated under reduced pressure, yielding 8-(3-trifluoromethylphenoxy)-1,4-dioxaspiro[4.5]decane.

Workup

  1. additionUpon complete addition
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux where it
  4. stirringis stirred for about four hours
  5. temperatureThe reaction mixture is cooled
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e573c6fd15264f19beb597465b5a674a
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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