Acetyl chloride → 3-Acetyl-2-hydroxy-5-methylbenzoic acid

HRID 983804

反応式

HRID 983804 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:9][C:10]1[CH:18]=[C:14]([C:15]([OH:17])=[O:16])[C:13]([OH:19])=[CH:12][CH:11]=1>C(Cl)Cl.CCOCC>[C:1]([C:12]1[CH:11]=[C:10]([CH3:9])[CH:18]=[C:14]([C:15]([OH:17])=[O:16])[C:13]=1[OH:19])(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 69735-Methylsalicylic acidHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 106793353-Acetyl-2-hydroxy-5-methylbenzoic acid

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

Acetyl chloride (14.7 ml, 5 eq.) is added slowly to an ice cooled suspension of AlCl3 (27.7 g, 5 eq.) in dry CH2Cl2 (125 ml). The reaction is stirred until most of the solid is dissolved, then 5-methyl salicylic acid 236 (6.31 g, 41 mmol) is added. The reaction is stirred at 0° C. for 1.5 hr, then at room temperature for 1.5 hr. The reaction is poured onto ice, diluted with Et2O, and washed with water, brine, dried (MgSO4). Concentration in vacuo afforded a slowly crystallizing oil. Recrystallization (CH2Cl2/hexanes) yielded pure 3-Acetyl-5-methyl salicylic acid (Example 529, Table IIIa) as 3.29 g of off white powder (41% recrystallized yield).

後処理

  1. temperaturecooled
  2. dissolutionis dissolved
  3. stirringThe reaction is stirred at 0° C. for 1.5 hr
  4. additionThe reaction is poured onto ice
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. concentrationConcentration in vacuo
  8. customafforded
  9. customa slowly crystallizing oil
  10. customRecrystallization (CH2Cl2/hexanes)

出典と根拠

ORDレコード
ord-af66025249be4d2b8ad6d66c1ce6e493
出典データセット
uspto-grants-2005_03
特許番号
US06867200B1

関連ノート

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