Hydrochloric Acid → HCID 18659296, compound

HRID 274891Notes

Reaction equation

HRID 274891 reaction equation
[OH-].[Na+].[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](/[C:16]1[CH2:17][O:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:21][CH:20]=2)\[CH3:15])=[CH:5]\[C:6]([O:8]CC)=[O:7].Cl>C(O)C.O>[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](/[C:16]1[CH2:17][O:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[CH:21][CH:20]=2)\[CH3:15])=[CH:5]\[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9952152HCID 9952152, compound

Product 1

HCID 18659296HCID 18659296, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

44 ml of 35% sodium hydroxide are added to a solution of 7.34 g (19 mmol) of the ester obtained in Example 25 in a mixture of 310 ml of ethanol and 140 ml of distilled water. The reaction mixture is then refluxed for 2 hours. The solution, cooled to +10° C., is acidified to pH 4 by means of a 4N hydrochloric acid solution. After the addition of 80 ml of water, the mixture is stirred at +10° C. for one hour. After filtration, the solid is rinsed with water and dried in a vacuum oven at 70° C. over phosphoric acid. Recrystallisation from ethanol yields 4.6 g of a yellow solid.

Workup

  1. temperatureThe reaction mixture is then refluxed for 2 hours
  2. temperatureThe solution, cooled to +10° C.
  3. filtrationAfter filtration
  4. washthe solid is rinsed with water
  5. dry with materialdried in a vacuum oven at 70° C. over phosphoric acid
  6. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-470de3a8fc424e3fb00f28cb43eab20c
Source dataset
uspto-grants-1995_02
Patent number
US05391569

Reaction notes

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