Potassium Hydroxide → HCID 54573316, compound

HRID 978422Notes

Reaction equation

HRID 978422 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-bad8d3e774fb42779b34d5e1ada6241b
Source dataset
uspto-grants-1987_05
Patent number
US04665084

Reaction notes

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