Hydrochloric Acid → HCID 14533172, compound

HRID 2073426Notes

Reaction equation

HRID 2073426 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]([C:18]([F:21])([F:20])[F:19])[CH2:14][CH2:15][CH2:16][CH3:17])(=O)=O)=CC=1.[C:23]1([CH:30]=[CH:29][C:27]([OH:28])=[CH:26][CH:25]=1)[OH:24].[OH-].[Na+].Cl>C(O)CCC.O>[F:19][C:18]([F:20])([F:21])[CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][CH2:11][O:24][C:23]1[CH:30]=[CH:29][C:27]([OH:28])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 14798Sodium HydroxideHCID 14533171HCID 14533171, compound

Product 1

HCID 14533172HCID 14533172, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

0.39 g of the above-obtained 3-trifluorometylheptyl p-toluenesulfonate and 0.25 g of hydroquinone were dissolved in 1 ml of butanol. To the solution was added a solution of 0.07 g of sodium hydroxide in 2 ml of butanol, followed by 5 hours of stirring at 130° C. for reaction. Then, water and 1N-hydrochloric acid were added to the reaction solution, followed by extraction with diethyl ether. The ether solution was dried with sodium sulfate, and the solvent was distilled off. The product was then purified by thin layer chromatography with methylene as the developer to obtain 0.17 g (yield:54%) of p-(3trifluoromethylheptyloxy)phenol which showed: [α]D26 -2.8, [α]43526 -4.9 (c 1, methylene chloride).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. dry with materialThe ether solution was dried with sodium sulfate
  3. distillationthe solvent was distilled off
  4. customThe product was then purified by thin layer chromatography with methylene as the developer

Sources & evidence

ORD record
ord-e712713cba07470ca33c5d4a6914c554
Source dataset
uspto-grants-1990_04
Patent number
US04917817

Reaction notes

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