Toluene → 3-(3-Trifluoromethylphenyl)-2-propene-1-ol

HRID 410145Notes

Reaction equation

HRID 410145 reaction equation
CS(O)(=O)=[O:3].[F:6][C:7]([F:19])([F:18])[C:8]1[CH:9]=[C:10]([CH:14](O)[CH:15]=[CH2:16])[CH:11]=[CH:12][CH:13]=1.C1(C)C=CC=CC=1>O1CCCC1.O>[F:6][C:7]([F:19])([F:18])[C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH2:16][OH:3])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 210748221-(3-(Trifluoromethyl)phenyl)prop-2-en-1-ol

Product 1

HCID 545026543-(3-Trifluoromethylphenyl)-2-propene-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulphonic acid (59.4 g) was added to a solution of 1-[3-(trifluoromethyl)phenyl]prop-2-en-1-ol (50 g) in tetrahydrofuran (200 mL) and de-ionized water (100 mL) at room temperature. Reaction mixture was refluxed at 65° C. to 70° C. for about 20-22 hours. After completion of the reaction, de-ionized water (50 mL) and toluene (200 mL) were added to organic layer. Organic layer was separated and neutralized to pH 7.5-8.0 using solution of sodium bicarbonate (7%), and concentrated under vacuum to give 3-[3-(trifluoromethyl)phenyl]prop-2-en-1-ol as oil.

Workup

  1. customReaction mixture
  2. temperaturewas refluxed at 65° C. to 70° C. for about 20-22 hours
  3. additionwere added to organic layer
  4. customOrganic layer was separated
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-89a27b8b28014132a73458f13b5233f5
Source dataset
uspto-grants-2014_06
Patent number
US08759586B2

Reaction notes

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