Sulfuric Acid → Benzenepropanol, 3-(trifluoromethyl)-

HRID 1156851Notes

Reaction equation

HRID 1156851 reaction equation
[O:1]1[CH2:3][CH2:2]1.[Mg].Cl[CH2:6][C:7]1[CH:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:11][CH:12]=1.S(=O)(=O)(O)O>C(OCC)C>[F:14][C:13]([F:15])([F:16])[C:9]1[CH:8]=[C:7]([CH2:6][CH2:3][CH2:2][OH:1])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6354Ethylene OxideHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 5462224Magnesium

Product 1

HCID 18755618Benzenepropanol, 3-(trifluoromethyl)-Yield 73.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 57 g of oxirane in 120 ml of diethyl ether is added dropwise, at 0° to 10° C., to a Grignard solution prepared from 14.8 g of magnesium and 100 g of 3-(chloromethyl)benzotrifluoride in 450 ml of diethyl ether. The mixture is subsequently stirred at room temperature for 1 hour and 300 ml of 10% strength sulfuric acid are then added, while cooling with ice. The organic phase is collected and extracted twice more with diethyl ether and the combined organic phases are dried over magnesium sulfate and distilled. 76.7 g of 3-(3-trifluoromethylphenyl)propan-1-ol of b.p. 85° to 95° C. under 0.02 mm Hg are obtained.

Workup

  1. temperaturewhile cooling with ice
  2. customThe organic phase is collected
  3. extractionextracted twice more with diethyl ether
  4. dry with materialthe combined organic phases are dried over magnesium sulfate
  5. distillationdistilled

Sources & evidence

ORD record
ord-99f5f88d4c5145b1b9cdb1b53af527ab
Source dataset
uspto-grants-1982_06
Patent number
US04337267

Reaction notes

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