3-(3-Chlorophenylthio)-4-oxocyclohexaneacetic acid ethyl ester → 9-Chloro-1,2,3,4-tetrahydrodibenzothiophene-3-acetic acid ethyl ester

HRID 1856522Notes

Reaction equation

HRID 1856522 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][C:9](=O)[CH:8]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH2:7]1)[CH3:2]>O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:7][C:8]2[S:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=3[C:9]=2[CH2:10][CH2:11]1)[CH3:2]

Participants

3

Reactant 1

HCID 130651313-(3-Chlorophenylthio)-4-oxocyclohexaneacetic acid ethyl ester

Product 1

HCID 130651369-Chloro-1,2,3,4-tetrahydrodibenzothiophene-3-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 g. of polyphosphoric acid contained in a 1-l. three-necked flask, provided with a stirrer and condenser was added 8.0 g. of 3-(3-chlorophenylthio)-4-oxocyclohexaneacetic acid ethyl ester. The mixture was heated on a steam bath for 90 minutes and then poured into a mixture of 200 g. of ice and 200 ml. of water with stirring, which was continued until the dark oily complex was decomposed and a light yellow color appeared. The product was extracted twice with 200 ml. of ether. The ether extract was washed twice with 50 ml. of water and then with 50 ml. of saturated sodium bicarbonate solution. The solution was dried over anhydrous potassium carbonate and then filtered. The ether was removed on a steam bath in a rotary evaporator at atmospheric pressure, and the residue was distilled at reduced pressure. At 205°-220°/2 mm. a yield of 3.3 g. of 9-chloro-1,2,3,4-tetrahydrodibenzothiophene-3-acetic acid ethyl ester was obtained.

Workup

  1. customthree-necked flask, provided with a stirrer and condenser
  2. additionwas added 8.0 g
  3. temperatureThe mixture was heated on a steam bath for 90 minutes
  4. additionpoured into a mixture of 200 g
  5. extractionThe product was extracted twice with 200 ml
  6. extractionThe ether extract
  7. washwas washed twice with 50 ml
  8. dry with materialThe solution was dried over anhydrous potassium carbonate
  9. filtrationfiltered
  10. customThe ether was removed on a steam bath in a rotary evaporator at atmospheric pressure
  11. distillationthe residue was distilled at reduced pressure
  12. customAt 205°-220°

Sources & evidence

ORD record
ord-84d03eb035524032a25efc5e8ab16b36
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

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