Hydrochloric Acid → HCID 19782165, compound

HRID 36943Notes

Reaction equation

HRID 36943 reaction equation
C(C1C=C([C:16]2[C:21]3[CH:22]=[C:23]4[CH2:28][CH2:27][CH2:26][C:24]4=[CH:25][C:20]=3[O:19][C:18](=[O:29])[C:17]=2[C:30]([O:32]CC)=[O:31])C=C(C(C)(C)C)C=1O)(C)(C)C.[OH-].[K+].C(O)C.Cl>O>[O:29]=[C:18]1[C:17]([C:30]([OH:32])=[O:31])=[CH:16][C:21]2[CH:22]=[C:23]3[CH2:28][CH2:27][CH2:26][C:24]3=[CH:25][C:20]=2[O:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 19782167Ethyl 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g][1]benzopyran-3-carboxylate

Product 1

HCID 19782165HCID 19782165, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4-(3,5-di-tert-butyl-4-hydroxy -phenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta [g] [1]benzopyran-3-carboxylate (1.85 g), potassium hydroxide (1.12 g) and 80% ethanol (12 ml) was stirred at room temperature for 3 hours. The reaction mixture was then diluted with water, adjusted to pH4 with 6N HCl and extracted with ethyl acetate. The extract was washed with water and dried (MgSO4) and the solvent was distilled off to give crystals of 4-3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g] [1]benzopyran-3-carboxylic acid. The crystals were collected by filtration and washed with isopropyl ether (1.13 g, 64.9%). mp. 256°-260° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5d21506b53714853b794470788f3b250
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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