Potassium Carbonate → 1-Adamantyl 3,4-dichlorophenylthiomethyl ketone

HRID 259309

Reaction equation

HRID 259309 reaction equation
Br[CH2:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].[Cl:15][C:16]1[CH:17]=[C:18]([SH:23])[CH:19]=[CH:20][C:21]=1[Cl:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][C:16]1[CH:17]=[C:18]([S:23][CH2:2][C:3]([C:5]23[CH2:14][CH:9]4[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]4)[CH2:6]2)[CH2:12]3)=[O:4])[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 799643,4-DichlorobenzenethiolHCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketone

Product 1

HCID 214240441-Adamantyl 3,4-dichlorophenylthiomethyl ketone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-adamantyl bromomethyl ketone (1.3 g.), 1.1 g. of 3,4-dichlorothiophenol and 800 mg. of anhydrous potassium carbonate in 30 ml. of acetone are stirred at reflux overnight. The solvent is then removed and 60 ml. of water is added to the reaction mixture. The product is filtered off, washed with water and recrystallized from methanol to yield 1-adamantyl 3,4-dichlorophenylthiomethyl ketone, M.P. 105°-110.5° C.

Workup

  1. temperatureat reflux overnight
  2. customThe solvent is then removed
  3. additionof water is added to the reaction mixture
  4. filtrationThe product is filtered off
  5. washwashed with water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5fa6384611b3406fa60c6e11270986ca
Source dataset
uspto-grants-1977_07
Patent number
US04036975

Linked notes

Loading…