Hydrochloric Acid → 3-(Methoxycarbonyl)-5-methylbenzoic acid

HRID 1016203

반응식

HRID 1016203 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl[CH:15](Cl)C.S(Cl)(Cl)=O.CO.Cl>CN(C=O)C.C(=O)(O)[O-].[Na+]>[CH3:15][O:12][C:11]([C:4]1[CH:5]=[C:6]([CH:10]=[C:2]([CH3:1])[CH:3]=1)[C:7]([OH:9])=[O:8])=[O:13]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 63651,1-DichloroethaneHCID 24386Thionyl ChlorideHCID 681375-Methylisophthalic acid

생성물 1

HCID 72108363-(Methoxycarbonyl)-5-methylbenzoic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 516892Sodium Bicarbonate용매

실험 절차

5-Methylisophthalic acid (1.21 g, 6.5 mmol), dichloroethane (20 mL), DMF (3 drops), and thionyl chloride (2.42 g, 20 mmol) was heated to 80° C. for 4 hrs. The reaction was concentrated to dryness and a solution of MeOH (208 mg, 6.5 mmol) was added slowly and the reaction was stirred overnight at rt. 1 N Hydrochloric acid (10 mL) was added and reaction stirred for 1 hr. The pH was adjusted with sat'd sodium bicarbonate (50 mL) and the aqueous solution was extracted with methylene chloride to remove the diester. The aqueous portion was then acidified with 1 N HCl and extracted with methylene chloride/MeOH 95:5. The organic extracts were dried over sodium sulfate, filtered, concentrated, and the product was isolated via preparative reverse-phase HPLC.

후처리

  1. concentrationThe reaction was concentrated to dryness
  2. customreaction
  3. stirringstirred for 1 hr
  4. extractionthe aqueous solution was extracted with methylene chloride
  5. customto remove the diester
  6. extractionextracted with methylene chloride/MeOH 95:5
  7. dry with materialThe organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe product was isolated via preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-329a9160cac24fd3be89323743149f7a
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985861B2

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