Sulfuric Acid → Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

HRID 736488

Reaction equation

HRID 736488 reaction equation
OS(O)(=O)=O.[O:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[CH2:8][CH2:7]1.[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][CH:21]=1>C(O)(=O)C>[O:16]=[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:6][CH2:7][C:8]1=[CH:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([O:18][CH3:17])=[O:28])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15294Methyl 4-FormylbenzoateHCID 68110Chromanone

Product 1

HCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoateYield 82.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated H2SO4 (2 ml) was slowly added to a solution of 4-chromanone (2.00 g, 13.50 mmol) and methyl4-formylbenzoate (2.11 g, 12.86 mmol) in glacial acetic acid. The reaction mixture was stirred 16 h at room temperature. The solvent was concentrated to half volume the resulting precipitate was filtered and rinsed with ethyl acetate to afford the title compound 260 (3.11 g, 82%) as a purple solid. 1H NMR: (DMSO) δ (ppm): 8.05 (d, J=8.2 Hz, 2H), 7.90 (d, J=7.6 Hz, 1H), 7.79 (s, 1H), 7.64-7.59(m, 3H), 7.15 (dd, J=7.6, 7.6 Hz, 1H), 7.07 (d, J=8.2 Hz, 1H), 5.43 (s, 2H), 3.89 (s, 3H).

Workup

  1. concentrationThe solvent was concentrated to half volume the resulting precipitate
  2. filtrationwas filtered
  3. washrinsed with ethyl acetate

Sources & evidence

ORD record
ord-3b20b036b159481ab259672fc3ba7427
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Linked notes

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