2-Methylresorcinol → 2H-1-Benzopyran-2-one, 7-hydroxy-8-methyl-4-(trifluoromethyl)-

HRID 1708209Notes

Reaction equation

HRID 1708209 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].[F:10][C:11]([F:21])([F:20])[C:12](=O)[CH2:13][C:14](OCC)=[O:15].C(=O)(O)[O-].[Na+]>O>[F:10][C:11]([F:21])([F:20])[C:12]1[C:5]2[C:3](=[C:2]([CH3:1])[C:8]([OH:9])=[CH:7][CH:6]=2)[O:4][C:14](=[O:15])[CH:13]=1

Participants

5

Reactant 3

HCID 118432-MethylresorcinolHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 54153912H-1-Benzopyran-2-one, 7-hydroxy-8-methyl-4-(trifluoromethyl)-Yield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slurry of 2-methylresorcinol (12.4 g, 0.100 mole) and ethyl 4,4,4-trifluoroacetoacetate (18.4 g, 0.100 mole) was added slowly to 100 ml of ice cold sulfuric acid with vigorous stirring. After completion of addition, the solution was allowed to warm to room temperature and was subsequently stirred for 24 hours. The reaction mixture was then slowly added to 500 ml of ice water (300 g ice and 200 ml water) with vigorous stirring. The desired product precipitated from the solution as a light pink solid. The solid was then isolated by vacuum filtration, transferred to a 500 ml beaker, 200 ml of water was added to achieve a slurry and the pH was adjusted to 6 with sodium bicarbonate. The solid was then filtered and recrystallized from ethanol-water to yield 19.5 g (80%) of the desired product. The melting point of the product was 197°-198 ° C.

Workup

  1. additionAfter completion of addition
  2. customThe desired product precipitated from the solution as a light pink solid
  3. customThe solid was then isolated by vacuum filtration
  4. additionwas added
  5. filtrationThe solid was then filtered
  6. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-a699911c0fdb49b2a5abb77f99e75293
Source dataset
uspto-grants-1994_10
Patent number
US05356929

Reaction notes

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