Hydrochloric Acid → HCID 70292399, compound

HRID 963531Notes

Reaction equation

HRID 963531 reaction equation
C(N[C:5](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=3[CH:18]=2)=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])(=O)C.Cl.C([OH:34])C>O>[OH:34][C:5](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:23]([CH3:27])([CH3:28])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=3[CH:18]=2)=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 54101352HCID 54101352, compound

Product 1

HCID 70292399HCID 70292399, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.6 g of (4 mmol) of α-acetamido-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyloxy)cinnamic acid, 25 ml of concentrated hydrochloric acid and 25 ml of ethyl alcohol were introduced into a round-bottomed flask and the mixture was heated at reflux for eight hours. The reaction medium was poured into water and extracted with ethyl acetate, and the organic phase was decanted, washed with water, dried over magnesium sulfate and evaporated. The residue obtained was triturated in a mixture of hexane and ethyl ether (80:20) and the mixture was filtered. 1.06 g (72%) of the expected acid was recovered, having a melting point of 207°-10° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for eight hours
  3. extractionextracted with ethyl acetate
  4. customthe organic phase was decanted
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue obtained
  9. customwas triturated in a mixture of hexane and ethyl ether (80:20)
  10. filtrationthe mixture was filtered
  11. custom1.06 g (72%) of the expected acid was recovered

Sources & evidence

ORD record
ord-0b52b79a8cb64067928dde89d3f0f88e
Source dataset
uspto-grants-1998_06
Patent number
US05763487

Reaction notes

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