Water → 4-Methoxy-3-sulfanylbenzoic acid

HRID 356943노트

반응식

HRID 356943 반응식
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])(=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.O1CCOCC1>C1(C)C=CC=CC=1>[SH:2][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 312751,4-DioxaneHCID 38548883-(Chlorosulfonyl)-4-methoxybenzoic acid

생성물 1

HCID 124257504-Methoxy-3-sulfanylbenzoic acid

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 3-chlorosulfonyl-4-methoxybenzoic acid (4.76 g; that is repared as described in Reference Example 44) in dry toluene (500 mL) stirred at room temperature is treated with triphenylphosphine (19.9 g) in one portion. The mixture is stirred and heated at 80° C. overnight, and then it is cooled, and treated with water (25 mL) and dioxane (25 mL), and the resulting solution is heated on a steam bath for 1 hour. The reaction mixture is allowed to cool to room temperature, and the organic layer is collected and concentrated. The resulting residue is partitioned between ethyl acetate (200 mL) and aqueous sodium hydroxide solution (500 mL; 2 N). The aqueous layer is separated, acidified by treatment with concentrated hydrochloric acid, and extracted with ethyl acetate (100 mL). The extract is washed with water (100 mL), dried over magnesium sulfate and concentrated, to give 3-mercapto-4-methoxybenzoic acid in the form of a white solid (3.4 g), m.p. 208°-210° C.

후처리

  1. stirringThe mixture is stirred
  2. temperatureheated at 80° C. overnight
  3. temperatureit is cooled
  4. temperaturethe resulting solution is heated on a steam bath for 1 hour
  5. temperatureto cool to room temperature
  6. customthe organic layer is collected
  7. concentrationconcentrated
  8. customThe resulting residue is partitioned between ethyl acetate (200 mL) and aqueous sodium hydroxide solution (500 mL; 2 N)
  9. customThe aqueous layer is separated
  10. extractionextracted with ethyl acetate (100 mL)
  11. washThe extract is washed with water (100 mL)
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5e8b2fbe275b4ec49b3954ed6a4273cf
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840724

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