Acetyl chloride → 4-(Acetoxymethyl)benzoic acid

HRID 411782ノート

反応式

HRID 411782 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-bd2bf2d02ab64519a5da2a2809b8859d
出典データセット
uspto-grants-2003_05
特許番号
US06559256B2

反応ノート

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