Hydrochloric Acid → HCID 53950594, compound

HRID 435068Notes

Reaction equation

HRID 435068 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:6][CH:5]([O:7]COCCOC)[C:4]([CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:14][CH3:15])[O:3]1.CO.Cl>C(OCC)C>[CH3:25][C:2]1([CH3:1])[CH2:6][CH:5]([OH:7])[C:4]([CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:14][CH3:15])[O:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 57055016HCID 57055016, compound

Product 1

HCID 53950594HCID 53950594, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The compound of Example 25 (3.85 g) was added to methanol (50 ml) containing 0.6 ml of 36% hydrochloric acid and the resulting mixture was refluxed for 21/2 hours. The mixture was then cooled and the methanol was evaporated to give an oily residue. This residue was dissolved in diethyl ether, washed with brine, dried over magnesium sulphate and evaporated to give 2.64 g (91.7%) of the pure desired product. This product was shown to be pure, and to consist of a mixture of isomers, by thin layer chromatography.

Workup

  1. temperaturethe resulting mixture was refluxed for 21/2 hours
  2. temperatureThe mixture was then cooled
  3. customthe methanol was evaporated
  4. customto give an oily residue
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-3d82e25df69342dc98ca7b4716f696d2
Source dataset
uspto-grants-1983_08
Patent number
US04400198

Reaction notes

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