Hydrochloric Acid → HCID 10110719, compound

HRID 636896Notes

Reaction equation

HRID 636896 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:11][CH:10]=[C:9](/[CH:12]=[CH:13]\[C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]2[CH:7]=[C:6](/[CH:18]=[CH:19]/[C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].Cl>O1CCCC1.C(O)C.O>[CH3:1][C:2]1([CH3:30])[CH2:11][CH:10]=[C:9](/[CH:12]=[CH:13]\[C:14]([CH3:15])([CH3:16])[CH3:17])[C:8]2[CH:7]=[C:6](/[CH:18]=[CH:19]/[C:20]3[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)[CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59942730HCID 59942730, compound

Product 1

HCID 10110719HCID 10110719, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[(E)-(5,6-dihydro-5,5-dimethyl-8-((Z)-3,3-dimethyl-1-buten-1-yl)-2-naphthalenyl)ethenyl]benzoate (3.0 g, 7.49 mmol) in tetrahydrofuran (60 mL) and ethanol (30 mL) was treated with 4N sodium hydroxide (9.36 mL, 37.6 mmol) and stirred for 30 hours. The reaction mixture was diluted with water and acidified to pH 2 with concentrated hydrochloric acid. The acid precipitated and was extracted into ethyl acetate. The organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude residue was dissolved in dichloromethane (75 mL) and ethanol (50 mL), filtered through a sintered glass and the filtrate was concentrated. The title material precipitated and was collected and dried to give a white solid (2.455 g, 85%).

Workup

  1. customThe acid precipitated
  2. extractionwas extracted into ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude residue was dissolved in dichloromethane (75 mL)
  8. filtrationethanol (50 mL), filtered through a sintered glass
  9. concentrationthe filtrate was concentrated
  10. customThe title material precipitated
  11. customwas collected
  12. customdried

Sources & evidence

ORD record
ord-a52fc334437f4c509b551c479408d724
Source dataset
uspto-grants-2001_02
Patent number
US06194601B1

Reaction notes

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