Hydrochloric Acid → 4-(2-Hydroxyethyl-mercapto)-benzophenone

HRID 1277849Notes

Reaction equation

HRID 1277849 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[SH:16][CH2:17][CH2:18][OH:19].C([O-])([O-])=O.[K+].[K+].Cl>CCOCC.O.CC(CC)=O>[OH:19][CH2:18][CH2:17][S:16][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 15672-MercaptoethanolHCID 86534-ChlorobenzophenoneHCID 11430Potassium Carbonate

Product 1

HCID 219508394-(2-Hydroxyethyl-mercapto)-benzophenone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

11.2 g (0.05 mol) of 4-chlorobenzophenone, 4.3 g (0.055 mol) of 2-mercaptoethanol, 13.8 g (0.1 mol) of calcined K2CO3 and 15 ml of ethyl methyl ketone are warmed (under reflux) for 16 hours under nitrogen. 50 ml of water are poured over the cooled reaction mixture and the resulting mixture is acidified with HCl. The product is taken up in ether. The ether layer is washed with water, dried over Na2SO4 and concentrated. The product, which in this case also is obtained in the form of an oil, crystallises on standing. It is boiled up in hexane as described under (a). Yield: 10.1 g (77%). Melting point 49°-51°.

Workup

  1. temperature(under reflux) for 16 hours under nitrogen
  2. washThe ether layer is washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe product, which in this case also is obtained in the form of an oil
  6. customcrystallises

Sources & evidence

ORD record
ord-6676bc73e95240d192bf76872ac1975a
Source dataset
uspto-grants-1981_07
Patent number
US04279721

Reaction notes

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