Hydrochloric Acid → 3,5-Dimethyl-2-(2-propen-1-yl)phenyl 2,2,2-trifluoroethyl ether

HRID 352353Notes

Reaction equation

HRID 352353 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:5]([CH2:12][CH:13]=[CH2:14])=[C:6]([OH:11])[CH:7]=[C:8]([CH3:10])[CH:9]=1.S(C1C=CC(C)=CC=1)(O[CH2:19][C:20]([F:23])([F:22])[F:21])(=O)=O.Cl>CN1CCCC1=O.O>[F:21][C:20]([F:23])([F:22])[CH2:19][O:11][C:6]1[CH:7]=[C:8]([CH3:10])[CH:9]=[C:4]([CH3:3])[C:5]=1[CH2:12][CH:13]=[CH2:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 2596542-Allyl-3,5-dimethylphenol

Product 1

HCID 227093213,5-Dimethyl-2-(2-propen-1-yl)phenyl 2,2,2-trifluoroethyl ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

17 g of sodium hydroxide were metered into a mixture of 50 g of 3,5-dimethyl-2-(2-propen-1-yl)-phenol (C) and 86 g of 2,2,2-trifluoroethyl tosylate in 450 ml of N-methylpyrrolidone at 120° C. Stirring was continued for 16 hours at 120° C., and the mixture was subsequently poured into 21 of water. The pH was brought to 2 using 6N hydrochloric acid, and the mixture was extracted using dichloromethane. The combined organic phases were dried over sodium sulphate, the solvent was removed in vacuo, and the residue was distilled. This gave 32 g (43% of theory) of 3,5-dimethyl-2-(2-propen-1-yl)phenyl 2,2,2-trifluoroethyl ether of a boiling point of 100° C. at 1 mbar.

Workup

  1. extractionthe mixture was extracted
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. customthe solvent was removed in vacuo
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-97fbc4371dd84716998068f70926ab25
Source dataset
uspto-grants-2004_06
Patent number
US06746990B2

Reaction notes

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