p-Toluenesulfonic acid → HCID 12391648, 화합물

HRID 1156086

반응식

HRID 1156086 반응식
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[CH2:3]1.[S:11]1[CH:15]=[CH:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[S:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:6]1[C:7](=[O:8])[CH2:9][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]=1[OH:5]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 31358DimedoneHCID 1368802,3-Dihydrothiophene

생성물 1

HCID 12391648HCID 12391648, 화합물

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of 7 parts of dimedone, 7 parts of 2,3-dihydrothiophene, 150 parts by volume of benzene and 0.7 parts of p-toluenesulfonic acid was refluxed by heating while stirring for 1 hour and 30 minutes and then allowed to stand at room temperature for 12 hours. The reaction mixture was washed with 50 parts by volume of water and then treated three times with 50 parts by volume of a 10% aqueous solution of sodium hydroxide. The aqueous layer was collected and the pH was adjusted to 2.0 with the addition of 6 N hydrochloric acid while maintaining the temperature thereof below 10° C. The light yellow 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 (1:1) as a spreading agent to obtain 2-(2-tetrahydrothienyl)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one in a form of colorless fine crystals. The melting point was 97° to 99° C. The yield was 8 parts.

후처리

  1. temperaturewas refluxed
  2. temperatureby heating
  3. waitto stand at room temperature for 12 hours
  4. washThe reaction mixture was washed with 50 parts by volume of water
  5. additiontreated three times with 50 parts by volume of a 10% aqueous solution of sodium hydroxide
  6. customThe aqueous layer was collected
  7. additionthe pH was adjusted to 2.0 with the addition of 6 N hydrochloric acid
  8. temperaturewhile maintaining the temperature
  9. custombelow 10° C
  10. customThe light yellow colored crystals thus deposited were collected
  11. custompurified
  12. additioncontaining a silica gel using
  13. additiona solvent mixture of chloroform and benzene (1:1) as a spreading agent

출처 및 근거

ORD 기록
ord-c5c81e24990d47a69c0070016df8ccff
출처 데이터셋
uspto-grants-1982_06
특허 번호
US04334010

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