Acetic Acid → 2,6-Dichloro-2',3'-dihydroxy-4'-methoxy-6'-methyl-benzophenone

HRID 361967

반응식

HRID 361967 반응식
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH3:14])=[C:8]([O:15]C)[C:7]=1[O:17]C)=[O:5].Br.C(O)(=O)C>O>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH3:14])=[C:8]([OH:15])[C:7]=1[OH:17])=[O:5]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 227199532,6-Dichloro-2',3',4'-trimethoxy-6'-methyl-benzophenone

생성물 1

HCID 545695512,6-Dichloro-2',3'-dihydroxy-4'-methoxy-6'-methyl-benzophenone

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

A mixture of 2,6-dichloro-2',3',4'-trimethoxy-6'-methyl-benzophenone (1.78 g; 5 mmol) hydrobromic acid (7.5 ml; 30% in acetic acid) and acetic acid (7.5 ml) is stirred at 75° C. for 2 hours. Water is added and the mixture extracted with methylenechloride. The extract is washed with waterand shaken with 2N sodium hydroxide. The alcaline solution is acidified with hydrochloric acid, the separated compound dissolved in methylenechloride and the solution washed with water. After evaporation ofthe solvent purification is carried out by chromatography (flash column, filled with 36 g of silicagel; elution with 500 ml of petrolether/ethylacetate (4:1; v/v) and 250 ml of petrolether/ethylacetate(1:1; v/v)). the fraction containing the compound is concentrated, the compound crystallized. The yellow crystals are washed with petrolether andsucked off; 0.64 g (39% y), mp. 182° C.

후처리

  1. extractionthe mixture extracted with methylenechloride
  2. washThe extract is washed with waterand
  3. stirringshaken with 2N sodium hydroxide
  4. dissolutionthe separated compound dissolved in methylenechloride
  5. washthe solution washed with water
  6. customAfter evaporation ofthe solvent purification
  7. additionis carried out by chromatography (flash column, filled with 36 g of silicagel; elution with 500 ml of petrolether/ethylacetate (4:1; v/v) and 250 ml of petrolether/ethylacetate(1:1; v/v))
  8. additionthe fraction containing the compound
  9. concentrationis concentrated
  10. customthe compound crystallized
  11. washThe yellow crystals are washed with petrolether

출처 및 근거

ORD 기록
ord-f2bc4d1e56aa4859abea606d965acb6e
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866722

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