Potassium Hydroxide → HCID 54420220, compound

HRID 745292Notes

Reaction equation

HRID 745292 reaction equation
[CH:1](=[C:8]1[C:21]2[O:20][C:19]3[C:14](=[CH:15][C:16]([C:22]([O:24]C)=[O:23])=[CH:17][CH:18]=3)[C:13](=[O:26])[C:12]=2[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH:1](=[C:8]1[C:21]2[O:20][C:19]3[C:14](=[CH:15][C:16]([C:22]([OH:24])=[O:23])=[CH:17][CH:18]=3)[C:13](=[O:26])[C:12]=2[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86740879HCID 86740879, compound

Product 1

HCID 54420220HCID 54420220, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-benzylidene-1,2,3,4-tetrahydro-9-oxo-9H-xanthen-7-carboxylic acid, methyl ester (1.2 g) was hydrolized by treatment with 1% KOH in 95% ethanol (19.5 ml) at reflux temperature for 15 minutes. After cooling and acidification with 37% HCl the precipitate was filtered and washed with methanol and then with water to give 1 g of 4-benzylidene-1,2,3,4-tetrahydro-9-oxo-9H-xanthen-7-carboxylic acid, m.p. 284°-286° C., NMR (CF3COOD) δppm: 2.12 (m) (2H, C-2 protons), 3.13 (m) (4H, C-1 and C-3 protons), 7.64 (m) (5H, phenyl protons), 8.14 (d) (1H, C-5 proton), 8.43 (bs) (1H, =CH--), 8.88 (dd) (1H, C-6 proton), 9.38 (d) (1H, C-8 proton).

Workup

  1. temperatureat reflux temperature for 15 minutes
  2. temperatureAfter cooling
  3. filtrationacidification with 37% HCl the precipitate was filtered
  4. washwashed with methanol

Sources & evidence

ORD record
ord-e1bd4d84f9c74e88be653532b8718ea7
Source dataset
uspto-grants-1986_07
Patent number
US04598090

Reaction notes

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