2-Methylbenzaldehyde → HCID 86740878, compound

HRID 978421Notes

Reaction equation

HRID 978421 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-785a83515edc4169aa5f7e14cce94a53
Source dataset
uspto-grants-1987_05
Patent number
US04665084

Reaction notes

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