Hydrochloric Acid → HCID 19015033, compound

HRID 247973Notes

Reaction equation

HRID 247973 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:7]([Cl:26])[CH:6]=1.[OH-].[K+].O.Cl>C(O)C>[Cl:26][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:27])=[O:2])[CH:10]=[CH:9][C:8]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 54402223HCID 54402223, compound

Product 1

HCID 19015033HCID 19015033, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 69.7 g of product from Example 63, 29.55 g of potassium hydroxide, 45 of water and 800 ml ethyl alcohol is heated at reflux temperature for 89 hours. The cooled solution was made acidic (pH 2) with concentrated hydrogen chloride; followed by heating to distill off the ethyl alcohol. The solution is diluted with diethyl ether and water. The organic layer is dried and concentrated in vacuo. The residue is recrystallized from methylene chloride/hexane to give 40.0 g of the desired product as colorless needles.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 89 hours
  3. temperatureby heating
  4. distillationto distill off the ethyl alcohol
  5. additionThe solution is diluted with diethyl ether and water
  6. customThe organic layer is dried
  7. concentrationconcentrated in vacuo
  8. customThe residue is recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-32f52239b4884d2082f70284f2b7ca7c
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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