HCID 53657949, compound → HCID 13065137, compound

HRID 1856526Notes

Reaction equation

HRID 1856526 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=O)[CH:8]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:7]1)=[O:5])[CH3:2]>O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][C:8]2[S:13][C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=3[C:9]=2[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 53657949HCID 53657949, compound

Product 1

HCID 13065137HCID 13065137, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 130 g. of polyphosphoric acid contained in a 500 ml. three-necked flask provided with a stirrer and condenser, was added 13 g. of 3-(4-methylphenylthio)-4-ketocyclohexanecarboxylic acid ethyl ester. The mixture was heated on a steam bath for 90 minutes and then poured onto a mixture of 200 g. of ice and 200 ml. of water. The mixture was stirred until the dark oily complex was decomposed, and a light yellow color appeared. The product was extracted with ether, and the solution then washed with water until it was neutral. After drying over anhydrous potassium carbonate, the ether was distilled off on the steam bath, and the residue was crystallized from methanol. The yield of 8-methyl-1,2,3,4-tetrahydrodibenzothiophene-3-carboxylic acid ethyl ester, m.p. 68°-69°, was 6 g.

Workup

  1. customthree-necked flask provided with a stirrer and condenser
  2. additionwas added 13 g
  3. temperatureThe mixture was heated on a steam bath for 90 minutes
  4. additionpoured onto a mixture of 200 g
  5. extractionThe product was extracted with ether
  6. washthe solution then washed with water until it
  7. dry with materialAfter drying over anhydrous potassium carbonate
  8. distillationthe ether was distilled off on the steam bath
  9. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-91a43ad134d3428ab044b0303b9184ea
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

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