Hydrochloric Acid → HCID 54347405, compound

HRID 745291Notes

Reaction equation

HRID 745291 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]2[CH2:15][CH2:16][CH2:17][C:3]1=2.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.C[O-].[Na+].Cl>CO>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[C:15]1[C:4]2[O:5][C:6]3[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][C:7]=3[C:2](=[O:1])[C:3]=2[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 86582-MethoxybenzaldehydeHCID 10942334Sodium MethoxideHCID 13375273HCID 13375273, compound

Product 1

HCID 54347405HCID 54347405, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

1,2,3,9-tetrahydro-9-oxo-cyclopenta[b][1]benzopyran-7-carboxylic acid, m.p. 273°-275° C. (1.6 g) was reacted with 2-methoxy-benzaldehyde (1 g) in methanol (60 ml) in the presence of sodium methylate (1.3 g) under stirring at 45° C. for 7 hours. After cooling, the reaction mixture was acidified with 37% HCl and the precipitate was filtered and washed with methanol and then with water until neutral. Crystallization from chloroform-ethanol gave 1.2 g of 3-(2-methoxy-benzylidene)-1,2,3,9-tetrahydro-9-oxo-cyclopenta[b][1]benzopyran-7-carboxylic acid, m.p. 291°-295° C., NMR (CH3COOD) δppm: 3.36 (bs) (4H, C-1 and C-2 protons), 4.09 (s) (3H, --OCH3), 7.09-7.87 (m) (4H, phenyl protons), 8.07 (d) (1H, C-5 proton), 8.41 (bs) (1H, =CH--), 8.76 (dd) (1H, C-6 proton), 9.28 (d) (1H, C-8 proton).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washwashed with methanol
  4. customCrystallization from chloroform-ethanol

Sources & evidence

ORD record
ord-ca487fc82b9045cdb9004e526ecadd52
Source dataset
uspto-grants-1986_07
Patent number
US04598090

Reaction notes

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