Hydrochloric Acid → HCID 54018478, compound

HRID 1609628Notes

Reaction equation

HRID 1609628 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:21])=[O:20])=[CH:15][CH:14]=1)[C:7]([CH3:22])=[C:6]2[CH2:23][C:24]([OH:26])=[O:25].C[O-].[Na+].C(=O)(O)[O-:31].[Na+].OO.Cl>C(#N)C.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:21])(=[O:31])=[O:20])=[CH:15][CH:14]=1)[C:7]([CH3:22])=[C:6]2[CH2:23][C:24]([OH:26])=[O:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 53948779HCID 53948779, compound

Product 1

HCID 54018478HCID 54018478, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

5-methoxy-2-methyl-1-(ρ-methylsulfonylbenzylidene)-3-indenyl acetic acid is prepared by the dissolving 0.03 moles of the sulfoxide in 25 ml. methanol, and 50 ml. acetonitrile are added. The solution is stirred at 0 C, and 0.03 moles of sodium methoxide are added dropwise. Stirring is continued, and 0.06 mole sodium bicarbonate is added as well a 0.06 moles of H2O2 (30% solution in water). The temperature is then dropped to -10 C, and stirring continued for 30 hours. At this time the NaHCO3 is filtered and washed on the filter with a few ml. of cold methanol. The washings are returned to the filtrate and the NaHCO3 is discarded. The filtrate is neutralized with 0.07 moles of HCl (concentrated HCl), partially evaporated to 50% of the original volume, and returned to the freezer for crystallization. Crystals of the sulfone derivative are collected. Additional sulfone can be collected from the mother liquor in a similar manner. (R1 = hydrogen; R2 =CH3 ; R3 =5-OCH 3 ; R4 =hydrogen; R5 =p-CH3SO2)

Workup

  1. additionare added dropwise
  2. additionThe temperature is then dropped to -10 C
  3. stirringstirring
  4. filtrationAt this time the NaHCO3 is filtered
  5. washwashed on the
  6. filtrationfilter with a few ml
  7. custompartially evaporated to 50% of the original volume
  8. customreturned to the freezer for crystallization
  9. customCrystals of the sulfone derivative are collected
  10. customAdditional sulfone can be collected from the mother liquor in a similar manner

Sources & evidence

ORD record
ord-29bc7519b1674c939836fc0b479599bb
Source dataset
uspto-grants-1995_03
Patent number
US05401774

Reaction notes

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