Potassium Hydroxide → HCID 54573316, compound

HRID 745290Notes

Reaction equation

HRID 745290 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH:4]=[C:5]1[C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][C:12]=3[C:13](=[O:14])[C:8]=2[CH2:7][CH2:6]1.[OH-].[K+]>C(O)C>[CH3:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH:4]=[C:5]1[C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:12]=3[C:13](=[O:14])[C:8]=2[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86740878HCID 86740878, compound

Product 1

HCID 54573316HCID 54573316, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-methyl-benzylidene)-1,2,3,9-tetrahydro-9-oxo-cyclopenta[b][1]benzopyran-7-carboxylic acid, methyl ester (3 g) was hydrolized by treatment with 1% KOH in 95% ethanol (59 ml) at reflux temperature for 15 minutes. After cooling, acidification with HCl and dilution with ice water, the precipitate was filtered and washed with water. Crystallization from dimethylformamide-ethanol gave 2.4 g of 3-(2-methyl-benzylidene)-1,2,3,9-tetrahydro-9-oxo-cyclopenta[b][1]benzopyran-7-carboxylic acid, m.p. 296°-298° C., NMR (CF3COOD) δppm: 2.59 (s) (3H, --CH3), 3.40 (bs) (4H, C-1 and C-2 protons), 7.38-7.87 (m) (4H, phenyl protons), 8.10 (d) (1H, C-5 proton), 8.30 (bs) (1H, =CH--), 8.80 (dd) (1H, C-6 proton), 9.30 (d) (1H, C-8 proton).

Workup

  1. temperatureat reflux temperature for 15 minutes
  2. temperatureAfter cooling
  3. filtrationacidification with HCl and dilution with ice water, the precipitate was filtered
  4. washwashed with water
  5. customCrystallization from dimethylformamide-ethanol

Sources & evidence

ORD record
ord-6681d39ce67c4848adb13ecd7186b318
Source dataset
uspto-grants-1986_07
Patent number
US04598090

Reaction notes

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