Hydrochloric Acid → HCID 69205197, compound

HRID 971030Notes

Reaction equation

HRID 971030 reaction equation
C([O:3][C:4](=[O:27])[CH:5]=[C:6]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([O:15][CH3:16])[CH:8]=1)C.[OH-].[K+].CO.Cl>O>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([C:6]([C:7]2[CH:8]=[C:9]([O:15][CH3:16])[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=2)=[CH:5][C:4]([OH:27])=[O:3])[CH:22]=[CH:21][C:20]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 69203667HCID 69203667, compound

Product 1

HCID 69205197HCID 69205197, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(3,4-Dimethoxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid ethyl ester (0.76 g, 2.05 mmol), potassium hydroxide (5 N, 8.10 ml, 20.52 mmol), methanol (6 ml), and H2O (1.5 ml) were mixed and stirred at rt for a couple of hours. The methanol was evaporated in vacuo leaving a clear solution, which was extracted with ether (2×60 ml) to get rid of the impurities. The aqueous phase was acidified with conc. HCl to pH around 23 to form a white precipitation, which was extracted with CH2Cl2 (2×100 ml), dried over MgSO4, filtered and concentrated to give 3-(3,4-dimethoxy-phenyl)-3-(3,5-dimethoxy-phenyl)-acrylic acid as a foamy solid (0.69 g, 98%); mp, 90-920C: 1HNMR (CDCl3) δ 6.90-6.75 (m, 4H, double bond protons and 2COOH), 6.50-6.24 (m, 12H, Ar), 3.92-3.75 (multiple singlets, 24H, 8OCH3), isomer ratio based on 1HNMR close to 43%:57%; Anal. Calcd. For C19H20O6: C, 66.27; H, 5.85. Found: C, 66.02; H, 5.81.

Workup

  1. customThe methanol was evaporated in vacuo
  2. customleaving a clear solution, which
  3. extractionwas extracted with ether (2×60 ml)
  4. customto get rid of the impurities
  5. customto form
  6. customa white precipitation, which
  7. extractionwas extracted with CH2Cl2 (2×100 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-694c9306b7414d56aa2e77e21eff6c24
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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