1-Indanone → Benzoic acid, 4-[(1,3-dihydro-1-oxo-2H-inden-2-ylidene)methyl]-

HRID 1174597Notes

Reaction equation

[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([OH:13])=[O:12].[OH-].[K+]>CCO>[O:10]=[C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[CH:18][C:17]1[CH:20]=[CH:21][C:14]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of indanone (2.00 g, 15.1 mmol) and 4-carboxybenzaldehyde (1.89 g, 12.6 mmol) in EtOH (10 ml) was added KOH (1.77 g , 31.5 mmol) at 0° C. The reaction mixture was stirred 30 min at 0° C. then at room temperature for 16 h. The solvent was evaporated and the residue was dissolved in water, acidified to pH 5 with HCl 1 M. The precipitate was filtered and rinsed with water to afford the title compound 273 (2.27 g, 57%) as a yellow solid. LRMS: 264.1 (Calc.); 265.0 (found).

Workup

waitat room temperature for 16 h
customThe solvent was evaporated
dissolutionthe residue was dissolved in water
filtrationThe precipitate was filtered
washrinsed with water

Sources & evidence

ORD record: ord-7ac0e42b17694bb4af23586e5a65f075
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838520B2

Reaction notes

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