Methanol → Methyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetate

HRID 1200190Notes

Reaction equation

HRID 1200190 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([OH:21])=[O:20])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:27]O>O>[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([O:21][CH3:27])=[O:20])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14650449HCID 14650449, compound

Product 1

HCID 14650461Methyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetateYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[2-(1-Cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetic acid (1.42 g) and conc. sulfuric acid (0.2 ml) were dded to methanol (30 ml) and the mixture was refluxed for 3 hours. Then, water was added. The mixture was extracted with ethyl acetate and the extracted layer was washed and dried. Ethyl acetate was distilled off under reduced pressure and the residue was recrystallized from hexane-ethyl acetate to obtain the title compound, m.p. 137°-138° C., yield 72%.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extracted layer was washed
  4. customdried
  5. distillationEthyl acetate was distilled off under reduced pressure
  6. customthe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-dfd0c026e62f4617a5822473dc5ea50d
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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