Methanol → HCID 19995392, compound

HRID 477292Notes

Reaction equation

HRID 477292 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:21]=[CH:20][C:19]4[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][C:15]([CH3:25])([CH3:24])[C:14]=4[CH:13]=3)[CH:10]=2)[C:5]([CH3:26])=[C:4]([C:27]([OH:29])=[O:28])[CH:3]=1.S(=O)(=O)(O)O.[CH3:35]O>>[CH3:35][O:28][C:27]([C:4]1[CH:3]=[C:2]([OH:1])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:21]=[CH:20][C:19]4[C:18]([CH3:22])([CH3:23])[CH2:17][CH2:16][C:15]([CH3:24])([CH3:25])[C:14]=4[CH:13]=3)[CH:10]=2)[C:5]=1[CH3:26])=[O:29]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 19995385HCID 19995385, compound

Product 1

HCID 19995392HCID 19995392, compound

Procedure

8.1 g (0.0209 mole) of the acid obtained in Example 5, 100 ml of methanol and 0.6 ml (0.0105 mole) of concentrated sulfuric acid are introduced in a balloon-flask, then heated by retort for 8 hours. After dry evaporation, water is added, neutralization is effected with sodium bicarbonate, followed with extraction with dichloromethane. After drying the organic phase on magnesium sulfate, the resulting solid is evaporated and then recrystallized in acetonitrile. Yield: 7.6 g (90.5%), fusion temperature: (224°-225° C.). RF: 0.5 [Merck silica plaques, the eluent being a mixture of ether-hexane (50:50)

Workup

  1. temperatureheated by retort for 8 hours
  2. customAfter dry
  3. customevaporation, water
  4. additionis added
  5. extractionfollowed with extraction with dichloromethane
  6. customAfter drying the organic phase on magnesium sulfate
  7. customthe resulting solid is evaporated
  8. customrecrystallized in acetonitrile
  9. custom(224°-225° C.)
  10. additionRF: 0.5 [Merck silica plaques, the eluent being a mixture of ether-hexane (50:50)

Sources & evidence

ORD record
ord-bbddd37aee174a4788c519f5cef39c21
Source dataset
uspto-grants-1989_12
Patent number
US04886907

Reaction notes

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