2-Methylbenzaldehyde → HCID 86740878, compound

HRID 745289Notes

Reaction equation

HRID 745289 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]2[CH2:16][CH2:17][CH2:18][C:3]1=2.[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.C[O-].[Na+]>CO>[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[C:16]1[C:4]2[O:5][C:6]3[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][C:7]=3[C:2](=[O:1])[C:3]=2[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 107222-MethylbenzaldehydeHCID 10942334Sodium MethoxideHCID 13375188HCID 13375188, compound

Product 1

HCID 86740878HCID 86740878, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,2,3,9-tetrahydro-9-oxo-cyclopenta[b][1]benzopyran-7-carboxylic acid, methyl ester, m.p. 156°-158° C. (5.1 g) was reacted with 2-methyl benzaldehyde (3.3 g) in methanol (80 ml) in the presence of sodium methylate (2.28 g) under stirring at room temperature for 20 hours. The precipitate was filtered and washed with methanol and then with water until neutral: crystallization from CH2Cl2 -methanol gave 5.2 g of 3-(2-methyl-benzylidene)-1,2,3,9-tetrahydro-9-oxo-cyclopenta[b][1]benzopyran-7-carboxylic acid, methyl ester, m.p. 203°-205° C.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with methanol
  3. customwith water until neutral: crystallization from CH2Cl2 -methanol

Sources & evidence

ORD record
ord-ab230fb8e2b24bf0bb8bf25e81cc2e1d
Source dataset
uspto-grants-1986_07
Patent number
US04598090

Reaction notes

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