4-(Methylsulfonyl)benzaldehyde → HCID 70286603, compound

HRID 377761

Reaction equation

HRID 377761 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10]([CH3:15])=[C:9]2[CH2:16][C:17]([O:19]C)=[O:18].[CH3:21][S:22]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)(=[O:24])=[O:23]>O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)/[C:11](=[CH:29]\[C:28]1[CH:31]=[CH:32][C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:26][CH:27]=1)/[C:10]([CH3:15])=[C:9]2[CH2:16][C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 2203764-(Methylsulfonyl)benzaldehydeHCID 10942334Sodium MethoxideHCID 53634864HCID 53634864, compound

Product 1

HCID 70286603HCID 70286603, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

25% methanolic sodium methoxide (16 ml, 2.0 equivalents) is treated with a solution of methyl 5-methoxy-2-methyl-3-indenylacetate (from Example 4, Part C) (8.7 g; 0.037 mol) and p-methylsulfonylbenzaldehyde, (6.3 g; 1.1 equivalent). The mixture is stirred at reflux under nitrogen for 2 hours. An equal volume of water is added slowly, and refluxing is continued for 30 min. The solution is cooled, is diluted with water and is washed with ether. Residual ether is blown off with nitrogen. The aqueous solution is acidified with 10% hydrochloric acid. The precipitated product is collected and is washed thoroughly with water. The crude product is crystallized from methanol to give (Z)-5-methoxy-2-methyl-1-(p-methylsulfonylbenzylidene)-3-indenylacetic acid.

Workup

  1. temperatureat reflux under nitrogen for 2 hours
  2. temperaturerefluxing
  3. temperatureThe solution is cooled
  4. washis washed with ether
  5. customThe precipitated product is collected
  6. washis washed thoroughly with water
  7. customThe crude product is crystallized from methanol

Sources & evidence

ORD record
ord-113586e271734fa8a1342d6dff985c0c
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Linked notes

Loading…