2-Hydroxy-p-toluic acid → HCID 19913828, compound

HRID 1110916Notes

Reaction equation

HRID 1110916 reaction equation
C([O:4][CH:5]([O:12][C:13](=[O:15])C)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C.[CH3:16]C1C=C(O)C(=CC=1)C(O)=O>S(=O)(=O)(O)O.C(O)(=O)C>[CH3:16][C:9]1[CH:10]=[CH:11][C:6]2[C:5](=[O:4])[O:12][CH2:13][O:15][C:7]=2[CH:8]=1

Participants

5

Reactant 2

HCID 57882-Hydroxy-p-toluic acidHCID 68489Benzylidene diacetate

Product 1

HCID 19913828HCID 19913828, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent2×

Procedure

61 g of benzal diacetate, 44.6 g of 4-methylsalicylic acid and 45 ml of acetic acid are combined and 5 drops of concentrated sulfuric acid are added and the mixture is heated under reduced pressure, allowing acetic acid to distill off. When the theoretical amount of acetic acid is collected (about 2.5 hours) the mixture is allowed to cool, diluted with ether and the ether solution washed with potassium carbonate solution, sodium bisulfite solution and dried over sodium sulfate. The ether is removed in vacuo and the resulting solid crystallized from ethyl acetate/hexane to give 7-methyl-1,3-benzodioxane-4-one.

Workup

  1. temperaturethe mixture is heated under reduced pressure
  2. distillationto distill off
  3. customWhen the theoretical amount of acetic acid is collected (about 2.5 hours) the mixture
  4. temperatureto cool
  5. additiondiluted with ether
  6. washthe ether solution washed with potassium carbonate solution, sodium bisulfite solution
  7. dry with materialdried over sodium sulfate
  8. customThe ether is removed in vacuo
  9. customthe resulting solid crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b1816cb85099418fa057a815fb5ffd7a
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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