Hydrochloric Acid → HCID 15552388, compound

HRID 429867Notes

Reaction equation

HRID 429867 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][CH:10]=[C:9](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:7]=[C:6](/[CH:20]=[CH:21]/[C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].Cl>O1CCCC1.C(O)C>[CH3:1][C:2]1([CH3:32])[CH2:11][CH:10]=[C:9](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:7]=[C:6](/[CH:20]=[CH:21]/[C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70192768HCID 70192768, compound

Product 1

HCID 15552388HCID 15552388, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a stirred solution of methyl 4-[(E)-[5,6-dihydro-5,5-dimethyl-8-[(E)-phenylethenyl]-2-naphthalenyl]ethenyl]benzoate (0.206 g, 0.49 mmol) in a mixture of tetrahydrofuran/ethanol (1:1, 2 mL) was added aqueous sodium hydroxide (5N, 0.98 mL, 4.90 mmol). The mixture was stirred overnight. Hydrochloric acid 1N was then added to precipitate the acid and ≈half of the volume of the solvents was evaporated. The white solid was filtered and washed with water. The solid was then dissolved in dichloromethane/ethanol, filtered and recrystallized from this mixture by evaporating the solvents. The title compound was obtained (0.149 g, 75%) as a white solid.

Workup

  1. customto precipitate the acid and ≈half of the volume of the solvents
  2. customwas evaporated
  3. filtrationThe white solid was filtered
  4. washwashed with water
  5. dissolutionThe solid was then dissolved in dichloromethane/ethanol
  6. filtrationfiltered
  7. customrecrystallized from this mixture
  8. customby evaporating the solvents

Sources & evidence

ORD record
ord-548e03237e464b1e8f376d7c5532e849
Source dataset
uspto-grants-2001_11
Patent number
US06319948B1

Reaction notes

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