Hydrochloric Acid → HCID 19901325, compound

HRID 2372652Notes

Reaction equation

HRID 2372652 reaction equation
[C:1]1([S:7]([CH3:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg]Br)C.[Cl:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].Cl.[Cl-].[NH4+]>C1COCC1.CCOCC>[Cl:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([OH:18])[CH2:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 107572-ChloroacetophenoneHCID 18369Methyl phenyl sulfoneHCID 25517Ammonium ChlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 19901325HCID 19901325, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

Methyl phenyl sulphone (12.5 g, 0.08 mole) dissolved in THF (150 cc) is added at ambient temperature to a molar solution (100 cc) of ethylmagnesium bromide. The mixture is stirred for 1 h and then cooled to -50° C. 2-Chloroacetophenone (12.5 g, 0.08 mole) dissolved in THF (150 cc) is run in and stirred for 2 h at -20° C. The mixture is poured into normal hydrochloric acid (200 cc) and ammonium chloride (6 g). It is reextracted with ether (3×50 cc), washed until neutral and dried over MgSO4. The crude is precipitated with heptane and recrystallized from isopropyl ether to give flocculent white crystals of 1-chloro-2-phenyl-3-phenylsulphonyl-2-propanol (6.5 g, 26%). Mp=110° C.

Workup

  1. stirringstirred for 2 h at -20° C
  2. washwashed until neutral and
  3. dry with materialdried over MgSO4
  4. customThe crude is precipitated with heptane
  5. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-260cb009e224453f893729038dd2c6a3
Source dataset
uspto-grants-1992_03
Patent number
US05100460

Reaction notes

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