Hydrochloric Acid → 2-Isopropyl-4-methoxy-5-trifluoromethyl-phenol

HRID 38396Notes

Reaction equation

HRID 38396 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1S(C1C=CC(C)=CC=1)(=O)=O)([CH3:3])[CH3:2].[OH-:26].[Na+].Cl>CO.O>[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[OH:26])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 670534811-Isopropyl-5-methoxy-2-(toluene-4-sulfonyl)-4-trifluoromethyl-benzene

Product 1

HCID 595987252-Isopropyl-4-methoxy-5-trifluoromethyl-phenolYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-Isopropyl-5-methoxy-2-(toluene-4-sulfonyl)-4-trifluoromethyl-benzene (0.40 g, 1.03 mmol) and NaOH (0.5 g, 12.5 mmol) in MeOH (5 ml) and H2O (5 ml) was heated at 90° C. for 2 hrs. The cooled reaction mixture was acidified with 3N HCl and extracted into methylene chloride. The combined extracts was dried with Na2SO4, filtered and concentrated to give desired 2-Isopropyl-4-methoxy-5-trifluoromethyl-phenol (0.194 g, 81%) as an oil.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted into methylene chloride
  3. dry with materialThe combined extracts was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a8055786d9ff467ea7b1aca6b4022246
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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