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

HRID 983804

Reaction equation

HRID 983804 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-af66025249be4d2b8ad6d66c1ce6e493
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Linked notes

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