Acetone → Methyl 4-(2-hydroxypropan-2-yl)benzoate

HRID 855296ノート

反応式

HRID 855296 の反応式
C([Mg]Cl)(C)C.I[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1.[CH3:17][C:18]([CH3:20])=[O:19]>C1COCC1>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:7]([C:18]([OH:19])([CH3:20])[CH3:17])=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 180AcetoneHCID 69273Methyl 4-iodobenzoateHCID 178418918HCID 178418918、化合物

生成物 1

HCID 18174533Methyl 4-(2-hydroxypropan-2-yl)benzoate収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

6.3 ml of a 2 molar solution of isopropylmagnesium chloride in THF (12 mmol) were added dropwise to a solution of 3 g methyl 4-iodobenzoate (11.5 mmol) in 30 ml THF at a temperature of −20° C. The reaction mixture was stirred for 1.5 h at −20° C., then 1.26 ml acetone (17 mmol) were added and the mixture was allowed to warm to rt. After 30 min at ambient temperature the reaction was quenched with methanol, poured into water and extracted with EtOAc. The combined extracts were washed with brine, dried with magnesium sulfate, filtered and concentrated. Chromatographic purification (silica gel; c-hexane/EtOAc 2:1) of the remaining residue yielded 1.64 g (74%) of 4-(1-hydroxy-1-methyl-ethyl)-benzoic acid methyl ester as a colorless liquid. 1H-NMR (CDCl3, 300 MHz): δ 1.60 (s, 6H), 3.91 (s, 3H), 7.56 (d, J=9 Hz, 1H), 8.01 (d, J=9 Hz, 1H).

後処理

  1. temperatureto warm to rt
  2. customAfter 30 min at ambient temperature the reaction was quenched with methanol
  3. additionpoured into water
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatographic purification (silica gel; c-hexane/EtOAc 2:1) of the remaining residue

出典と根拠

ORDレコード
ord-83dcde08e4e947499ed5ce30a49d1fd7
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

反応ノート

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