Water → HCID 14650436, compound

HRID 1200184Notes

Reaction equation

HRID 1200184 reaction equation
[CH:1]1([C:6](=[O:18])[CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=2O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.O>C(O)(=O)C>[CH:1]1([C:6]2[O:18][C:11]3[C:12]([CH3:16])=[CH:13][CH:14]=[CH:15][C:10]=3[C:8](=[O:9])[CH:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 14650432HCID 14650432, compound

Product 1

HCID 14650436HCID 14650436, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

1-Cyclopentyl-3-(2-hydroxy-3-methylphenyl)-1,3-propanedione (14 g) was dissolved in acetic acid (70 ml) and conc. sulfuric acid (3 ml) was added to the solution. The mixture was stirred at 100° C. for 1 hour. The reaction mixture was poured into cold water and extracted with ethyl acetate. The extract was washed with water, aqueous saturated sodium bicarbonate and then water and dried (MgSO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate (4:1)) to obtain the title compound (12.7 g) as crystals, yield 97.4%. The crystals were recrystallized from methanol to obtain prisms, m.p. 51°-52° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, aqueous saturated sodium bicarbonate
  3. dry with materialwater and dried (MgSO4)
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate (4:1))

Sources & evidence

ORD record
ord-8e3c1d708ef64385851c051d9c872196
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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