Potassium Hydroxide → HCID 19593538, compound

HRID 613836Notes

Reaction equation

HRID 613836 reaction equation
[C:1]1([CH2:11][C:12]([CH2:21][C:22]2[C:31]3[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)(C(OC)=O)[C:13]([O:15]C)=[O:14])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)CCC.O>[C:1]1([CH2:11][CH:12]([CH2:21][C:22]2[C:31]3[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)[C:13]([OH:15])=[O:14])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54556119HCID 54556119, compound

Product 1

HCID 19593538HCID 19593538, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A solution of 3.1 g (7.4 mmol) of dimethyl bis-(5,6,7,8-tetrahydro-1-naphthylmethyl)-malonate in 20 mL n-butanol was treated with a solution of 1.24 g (22 mmol) of potassium hydroxide (KOH) in 20 mL H2O and the solution heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in H2O and acidified with dilute HCl to the Congo red color change. The mixture was extracted with EtOAc and the EtOAc washed with 1N HCl, and then a saturated solution of NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave 2.03 g of the product. A small amount recrystallized from EtOAc/hexane had mp 144-146° C. The structure was confirmed by NMR spectroscopy.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. extractionThe mixture was extracted with EtOAc
  5. washthe EtOAc washed with 1N HCl
  6. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-de8e2648635946328add9fa56309b9ed
Source dataset
uspto-grants-1999_12
Patent number
US06008372

Reaction notes

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