Acetyl chloride → 4-(Acetoxymethyl)benzoic acid

HRID 896753ノート

反応式

HRID 896753 の反応式
C(N([CH2:6][CH3:7])CC)C.C(Cl)(=[O:10])C.[C:12]([O:15][CH2:16][CH3:17])(=[O:14])[CH3:13].[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[C:12]([O:15][CH2:16][C:17]1[CH:7]=[CH:6][C:19]([C:20]([OH:10])=[O:21])=[CH:18][CH:22]=1)(=[O:14])[CH3:13]

参加物

5

反応物 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl Acetate

生成物 1

HCID 70215904-(Acetoxymethyl)benzoic acid

反応条件

温度
0 °C

実験手順

Triethylamine (15.4 ml, 110.4 mmol) was added to a solution of aldehyde (2) (12.57 g, 92.4 mmol) in THF (50 ml) and cooled to 0° C. Acetyl chloride (7.91 g, 110.4 mmol) was then gradually added over 25 minutes, and the mixture was then left to stir for two hours at room temperature. After one hour, ethyl acetate (200 ml) was added and the solution washed with sodium carbonate (100 ml), HCl (17%, 50 ml) and water (100 ml) respectively. The organic layer was then dried over sodium sulfate and the solvent removed under reduced pressure to give an oil which crystallised when cooled. Re-crystallisation in methanol-hexane gave light yellow crystals.

後処理

  1. waitthe mixture was then left
  2. waitAfter one hour
  3. washthe solution washed with sodium carbonate (100 ml), HCl (17%, 50 ml) and water (100 ml) respectively
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customto give an oil which
  7. customcrystallised when
  8. temperaturecooled
  9. customRe-crystallisation in methanol-hexane gave light yellow crystals

出典と根拠

ORDレコード
ord-59fe703f5ca84420b9e17c5cae1f26e2
出典データセット
uspto-grants-2005_07
特許番号
US06919415B2

反応ノート

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