Ethanol → HCID 14650456, compound

HRID 1200188Notes

Reaction equation

HRID 1200188 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.[CH2:27](O)[CH3:28]>>[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([O:21][CH2:27][CH3:28])=[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

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14650449HCID 14650449, compound

Product 1

HCID 14650456HCID 14650456, compound

Procedure

[2-(1-Cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetic acid (2.0 g) was dissolved in ethanol (50 ml) and to the solution was added conc. sulfuric acid (0.5 ml). The mixture was heated under reflux for 5 hours. After dilution with water, the mixture was extracted with ethyl acetate and the extract was washed with water, dried (MgSO4) and concentrated under reduced pressure to obtain the title compound as crystals. The crystals were recrystallized from ethyl acetate to obtain prisms, yield 1.34 g (61.0%), m.p. 126°-127° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. extractionAfter dilution with water, the mixture was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90bb2b0bde91408a8b1e5f90916d1703
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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