Cyclohexane → 2-[[(Methoxyphenyl)methyl]thio]cyclopentanecarboxylic acid

HRID 638116

반응식

HRID 638116 반응식
C1([C:6](O)=[O:7])CCCC=1.COC1C=CC(CS)=CC=1.CO[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][S:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH:30]2[C:34]([OH:36])=[O:35])=[CH:23][CH:22]=1.C1CCCCC1>N1CCCCC1.C(O)(=O)C>[CH3:6][O:7][C:23]1[CH:22]=[CH:21][CH:26]=[CH:25][C:24]=1[CH2:27][S:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH:30]1[C:34]([OH:36])=[O:35]

참가 물질

7

반응물 4

HCID 8078CyclohexaneHCID 804074-Methoxy-alpha-toluenethiolHCID 959641-Cyclopentene-1-carboxylic acidHCID 136525392-[[(4-Methoxyphenyl)methyl]thio]cyclopentanecarboxylic acid

생성물 1

HCID 202532662-[[(Methoxyphenyl)methyl]thio]cyclopentanecarboxylic acid

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8082Piperidine용매

실험 절차

A solution of 1-cyclopentene carboxylic acid (1.68 g., 15 mmole) and p-methoxy-α-toluenethiol (2.17 ml., 15.6 mmole) in piperidine (3.9 ml.) is flushed with argon and heated under reflux, protected by a drying tube, for 12 hours. The mixture is then partitioned between ethyl ether (100 ml.) and 1N hydrochloric acid (3×40 ml.). The organic phase is stirred with activated charcoal (about 0.5 g.), dried (MgSO4), filtered through Celite, and concentrated in vacuo to an orange-yellow oil. This oil is recrystallized successively (3 times) from cyclohexane/hexane to yield 1.75 g. of 2-[[(4-methoxyphenyl)methyl]thio]cyclopentanecarboxylic acid as a tan, granular solid; m.p. 63°-66°. TLC (silica gel, cyclohexane:acetic acid, 8:1) Rf =0.23.

후처리

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe mixture is then partitioned between ethyl ether (100 ml.) and 1N hydrochloric acid (3×40 ml.)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through Celite
  6. concentrationconcentrated in vacuo to an orange-yellow oil
  7. customThis oil is recrystallized successively (3 times) from cyclohexane/hexane
  8. customto yield 1.75 g

출처 및 근거

ORD 기록
ord-dabd2255b2b84fada53ec72f1652c875
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560506

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