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

HRID 983804

반응식

HRID 983804 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-af66025249be4d2b8ad6d66c1ce6e493
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867200B1

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