Hydrochloric Acid → HCID 54201360, compound

HRID 1107132Notes

Reaction equation

HRID 1107132 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][C:13]([O:15]CC)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53688447HCID 53688447, compound

Product 1

HCID 54201360HCID 54201360, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing ethyl 3-(3,4-dimethoxyphenyl)-7-phenyl-2-heptenoate (0.9 g, 2.4 mmol) and 10% sodium hydroxide (10 mL) in ethanol (20 mL) is heated under reflux for 1 hour. The mixture is cooled and is added to aqueous HCl and is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo to provide 3-(3,4-Dimethoxyphenyl)-7-phenyl-2-heptenoic acid as an oil (0.7 g, 87% ) 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.48-1.60 (m, 2H), 1.60-1.80 (m, 2H), 2.58-2.69 (t, 2H), 3.10-3.20 (t, 2H), 3.90 (s, 6H), 6.08 (s, 1H), 6.80-6.90 (d, 1H), 6.90-6.98 (s, 1H), 6.98-7.09 (d, 1H), 7.09-7.32 (m, 5H); MS (EI) m/e 340 (M+).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe mixture is cooled
  4. extractionis extracted with ether
  5. washThe organic layer is washed with water
  6. dry with materialis dried over MgSO4
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-46f7e66aae2a43d59a604230177fb353
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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