Sodium Hydroxide → HCID 54453629, compound

HRID 1763075Notes

Reaction equation

HRID 1763075 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:16][CH:17]=[C:18]([Cl:20])[CH3:19])([CH2:13][CH2:14][CH3:15])[C:8]2=[O:12])=[CH:4][C:3]=1[CH:21](C(OCC)=O)[C:22]([O:24]CC)=[O:23].[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:16][CH:17]=[C:18]([Cl:20])[CH3:19])([CH2:13][CH2:14][CH3:15])[C:8]2=[O:12])=[CH:4][C:3]=1[CH2:21][C:22]([OH:24])=[O:23]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54492079HCID 54492079, compound

Product 1

HCID 54453629HCID 54453629, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Crude diethyl 2-[6,7-dichloro-2-(3-chloro-2-butenyl)-2,3-dihydro-1-oxo-2-propyl-1H-inden-5-yl]malonate (36.9 g, 0.075 mole) was refluxed with stirring in a mixture of ethanol (100 ml), water (100 ml) and sodium hydroxide (15 g) for 2 hours. The reaction mixture was cooled, diluted with water and extracted with hexane. The aqueous layer was acidified with hydrochloric acid and extracted with methylene chloride. The organic extracts were washed with water, dried over MgSO4 and concentrated under vacuum to obtain 17 g of product which after recrystallization from a mixture of methyl cyclohexane and butyl chloride melted at 111°-114° C. and was shown by HPLC to be a 95% trans, 5% cis mixture.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with hexane
  3. extractionextracted with methylene chloride
  4. washThe organic extracts were washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0f091094dd7946c98b055722e6e5e6b3
Source dataset
uspto-grants-1989_05
Patent number
US04835313

Reaction notes

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