Potassium Hydroxide → HCID 13746688, compound

HRID 1731624Notes

Reaction equation

HRID 1731624 reaction equation
[OH-].[K+].[SH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7]2.[C:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[C:18](I)[CH:17]=1)([OH:15])=[O:14]>[Cu]>[C:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[C:18]([S:3][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[CH2:9][CH2:8][CH2:7]3)[CH:17]=1)([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 49618532,3-dihydro-1H-indene-5-thiolHCID 13746687HCID 13746687, compound

Product 1

HCID 13746688HCID 13746688, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

To 50% aqueous potassium hydroxide solution (500 g) under argon was added 5-mercaptoindan (30.0 g, 0.2 mole) and copper powder (16.3 g). Then 4-carboxy-2-iodophenylacetic acid (38.25 g, 0.125 mole) was added with mechanical stirring and the reaction mixture was stirred under reflux (oil-bath 140°-145° C.) for 3 hours. The mixture was diluted with ice-water (800 ml), filtered, and the filtrate was treated with charcoal and refiltered. Acidification of the alkaline solution precipitated a solid which was collected, washed well with water and drained thoroughly on the filter. The solid was stirred with hexane (200 ml) to remove mercaptoindane and was refiltered to yield 33.55 g.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureunder reflux (oil-bath 140°-145° C.) for 3 hours
  3. filtrationfiltered
  4. additionthe filtrate was treated with charcoal
  5. customAcidification of the alkaline solution precipitated a solid which
  6. customwas collected
  7. washwashed well with water
  8. stirringThe solid was stirred with hexane (200 ml)
  9. customto remove mercaptoindane
  10. customto yield 33.55 g

Sources & evidence

ORD record
ord-89cd66ae9ee7474c85c27727f3e80c16
Source dataset
uspto-grants-1986_11
Patent number
US04622403

Reaction notes

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