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

HRID 1820273

反応式

HRID 1820273 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

HCID 72108363-(Methoxycarbonyl)-5-methylbenzoic acid

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f4eaf2cb7f14f58a105cd24c7c1963e
出典データセット
uspto-grants-2009_10
特許番号
US07601844B2

関連ノート

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