Hydrochloric Acid → HCID 18626563, compound

HRID 1859763Notes

Reaction equation

HRID 1859763 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:27]([O:29]CC)=[O:28])[O:26][CH2:25][C:11]3([C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:18][C:17]4[C:12]3=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[OH-].[K+].C(O)C.Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:27]([OH:29])=[O:28])[O:9][CH2:10][C:11]3([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[O:18][C:19]4[C:24]3=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:25][O:26]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 9932771HCID 9932771, compound

Product 1

HCID 18626563HCID 18626563, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.09 g (0.2 mmol) of the ester prepared in Example 77, Example [sic], 0.5 g (9 mmol) of KOH, 20 ml of ethanol and 10 ml of water is stirred at reflux for 3 h. After cooling, the reaction medium is acidified with concentrated HCl solution to pH=5 and extracted with ethyl acetate. The combined organic phases are dried over Na2SO4 and then evaporated. The residual oil is crystallized from a suitable solvent. 0.06 g of white solid is isolated (yield=64%). m.p.=244-246° C.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe residual oil is crystallized from a suitable solvent

Sources & evidence

ORD record
ord-c790f1a45372431a9f2c954c01a5a2e6
Source dataset
uspto-grants-2003_03
Patent number
US06528538B1

Reaction notes

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