Hydrochloric Acid → 2-[(3,4-Dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylic acid

HRID 1107129Notes

Reaction equation

HRID 1107129 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[C:16](=[CH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14][C:13]=2[C:26]([O:28]C)=[O:27])[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]([S:11][C:12]2[C:16](=[CH:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:15][CH2:14][C:13]=2[C:26]([OH:28])=[O:27])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69907819Methyl 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylate

Product 1

HCID 699076212-[(3,4-Dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylate (0.5 g, 1.2 mmol) and 10% sodium hydroxide (5 mL) in ethanol (10 mL) is heated under reflux for 4 hours. The mixture is cooled and is poured into aqueous HCl. The mixture is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo to provide 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylic acid (0.4 g, 85%): m.p. 146-8° C. Anal. (C23H26O4S) C,H,N: 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.10-1.70 (m, 5H), 1.83-2.02 (m, 1H), 2.32-2.41 (t, 2H), 2.60-2.72 (m, 3H), 3.84 (s, 3H), 3.90 (s, 3H), 6.69-6.75 (d, 1H), 6.94-7.00 (m, 2H), 7.00-7.10 (d, 2H), 7.18-7.32 (m, 3H); MS (EI) m/e 398 (M+).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe mixture is cooled
  4. extractionThe mixture is 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-cc3cbc8ba8f74c9e894b0ca18b16176f
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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