Toluene → Benzoic acid, 4-(acetylamino)-2-hydroxy-3-(2-propenyl)-, methyl ester

HRID 1650374Notes

Reaction equation

HRID 1650374 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])C=C.[C:19]1(C)[CH:24]=CC=C[CH:20]=1>>[CH2:24]([C:14]1[C:13]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[OH:4])[CH:19]=[CH2:20]

Participants

3

Reactant 2

HCID 1140TolueneHCID 10586690HCID 10586690, compound

Product 1

HCID 10800613Benzoic acid, 4-(acetylamino)-2-hydroxy-3-(2-propenyl)-, methyl ester

Procedure

A solution of 5 g (20.1 mmol) of the allyl ether from Example 19 in 20 ml of toluene is heated at 200° C. in a sealed tube for 24 hours. After cooling to room temperature a precipitate begins forming and the reaction mixture is cooled further to 0° C. The precipitate is filtered off and allowed to air dry, giving methyl 3-allyl-4-acetylaminosalicylate which can be used directly in the next step.

Workup

  1. custombegins forming
  2. temperaturethe reaction mixture is cooled further to 0° C
  3. filtrationThe precipitate is filtered off
  4. customto air dry

Sources & evidence

ORD record
ord-0a9abe035ae7407abfcee0954060758a
Source dataset
uspto-grants-1990_05
Patent number
US04924010

Reaction notes

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