Hydrochloric Acid → HCID 21459586, compound

HRID 1941016Notes

Reaction equation

HRID 1941016 reaction equation
[CH3:1][C:2]12[CH2:33][CH:5]([C:6]3([CH3:32])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([CH:16]([OH:31])[C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[CH:23]=[C:22]([C:27]([O:29]C)=[O:28])[CH:21]=[CH:20]5)[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2.[OH-].[Na+].Cl>CO>[CH3:1][C:2]12[CH2:33][CH:5]([C:6]3([CH3:32])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([CH:16]([OH:31])[C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[CH:23]=[C:22]([C:27]([OH:29])=[O:28])[CH:21]=[CH:20]5)[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21459581HCID 21459581, compound

Product 1

HCID 21459586HCID 21459586, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

898 mg (2.03 mmol) of the ester obtained in Example 6, in 25 ml of methanol, were treated with 2 g of sodium hydroxide. The reaction mixture was maintained under stirring for 48 hours. The reaction mixture was poured into ice-cold water, acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, filtered and evaporated to yield 951 mg (92%) of the expected compound, melting at 146°-148° C.

Workup

  1. temperatureThe reaction mixture was maintained
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b03db1fa66d54d66824bc26736eecbef
Source dataset
uspto-grants-1997_12
Patent number
US05702710

Reaction notes

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