Methyl anisate → 4-Methoxy-3-(2-methyl-benzoyl)-benzoic acid methyl ester

HRID 521502

反応式

HRID 521502 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[CH3:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17].[Sn](Cl)(Cl)(Cl)Cl>ClC1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[CH3:13])[CH:5]=1

参加物

5

反応物 3

HCID 8499Methyl anisateHCID 24287Tin tetrachloride2 回HCID 702762-Methylbenzoyl chloride

生成物 1

HCID 670766294-Methoxy-3-(2-methyl-benzoyl)-benzoic acid methyl ester収率 2.3%

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
140 °C

実験手順

4-Methoxybenzoic acid methyl ester (5.00 g, 30.1 mmol) and 2-methylbenzoyl chloride (4.88 g, 31.6 mmol) were dissolved in chlorobenzene (10 ml), tin(IV) chloride (9.41 g, 36.1 mmol) was added cautiously, and the mixture was heated to 140° C. for 3 h. The addition of the acid chloride and tin tetrachloride was repeated twice, and the mixture subsequently heated to 140° C. for 3 h each time. The mixture was poured onto 300 ml of ice/water and extracted with DCM. The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) and subsequently by RP HPLC (water/ACN gradient) to yield 200 mg of the title compound.

後処理

  1. temperaturethe mixture subsequently heated to 140° C. for 3 h each time
  2. extractionextracted with DCM
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel chromatography (HEP/EA gradient) and subsequently by RP HPLC (water/ACN gradient)

出典と根拠

ORDレコード
ord-25f12cb9926942ddae7c60be553fed9d
出典データセット
uspto-grants-2016_05
特許番号
US09328071B2

関連ノート

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