1,3-Cyclohexanedione, 5-phenyl- → HCID 12391651, compound

HRID 1156085Notes

Reaction equation

HRID 1156085 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH:16]1[CH2:20][CH2:19][CH2:18][S:17]1>C1C=CC=CC=1>[S:17]1[CH2:18][CH2:19][CH2:20][CH:16]1[C:10]1[C:11](=[O:13])[CH2:12][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C:9]=1[OH:14]

Participants

4

Reactant 2

HCID 5689621,3-Cyclohexanedione, 5-phenyl-HCID 12335980HCID 12335980, compound

Product 1

HCID 12391651HCID 12391651, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.0 parts of 5-phenyl-1,3-cyclohexanedione and 120 parts by volume of a 5% benzene solution of 2-chlorotetrahydrothiphene was refluxed by heating while stirring. After cooling to room temperature, the reaction mixture was washed with 40 parts by volume of water and then treated three times with 30 parts by volume of a 5% aqueous solution of sodium hydroxide. The aqueous layer was collected and washed with 30 parts by volume of ether. While maintaining the temperature of the solution below 10° C., the pH of the solution was controlled between 4 and 5 with the addition of 6 N hydrochloric acid. The light orange colored crystals thus deposited were collected and purified by passing through a column containing a silica gel using a solvent mixture of chloroform and benzene (5:1) as a spreading agent to obtain 2-(2-tetrahydrothienyl)-3-hydroxy-5-phenyl-2-cyclohexen-1-one in a form of colorless fine crystals. The melting point was 141° to 142° C. The yield was 2.4 parts.

Workup

  1. temperaturewas refluxed
  2. temperatureby heating
  3. washthe reaction mixture was washed with 40 parts by volume of water
  4. additiontreated three times with 30 parts by volume of a 5% aqueous solution of sodium hydroxide
  5. customThe aqueous layer was collected
  6. washwashed with 30 parts by volume of ether
  7. temperatureWhile maintaining the temperature of the solution below 10° C.
  8. additionthe pH of the solution was controlled between 4 and 5 with the addition of 6 N hydrochloric acid
  9. customThe light orange colored crystals thus deposited were collected
  10. custompurified
  11. additioncontaining a silica gel using
  12. additiona solvent mixture of chloroform and benzene (5:1) as a spreading agent

Sources & evidence

ORD record
ord-88ce6ff9ad2f41198051e9be80f02bbe
Source dataset
uspto-grants-1982_06
Patent number
US04334010

Reaction notes

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