Potassium Hydroxide → HCID 70432086, compound

HRID 1906922Notes

Reaction equation

HRID 1906922 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:13]=[C:12]([Cl:14])[C:11]2[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=2)[C:5]=1[CH2:16][CH2:17][CH:18](O)[CH2:19][CH:20]([OH:26])[CH2:21][C:22]([O:24]C)=[O:23]>O.CO.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:13]=[C:12]([Cl:14])[C:11]2[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=2)[C:5]=1[CH2:16][CH2:17][C@@H:18]1[O:24][C:22](=[O:23])[CH2:21][C@@H:20]([OH:26])[CH2:19]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 13826419HCID 13826419, compound

Product 1

HCID 70432086HCID 70432086, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of potassium hydroxide (0.1 g, 1.5 mmole) in water (2 ml) was added dropwise to a solution of methyl 7-(2,4,7-trichloronaphthalene-1-yl)-3,5-dihydroxyheptanoate (0.22 g, 0.7 mmole) in methanol (10 ml) with cooling (ice bath). The bath was removed and the reaction mixture stirred at room temperature for one hour and then concentrated in vacuo. The residue was diluted with ice and water, acidified with dilute aqueous HCl and extracted with ether. The ether extracts were combined, washed with water and brine and dried over MgSO4. The ether solution was filtered and concentrated in vacuo to give a yellow oil, which was taken up in toluene (75 ml). After heating at reflux for 4 hours, using a Soxhlet Apparatus containing molecular sieves, the toluene solution was concentrated in vacuo to give a viscous yellow oil (0.2 g). This material was chromatographed using a 30 mm flash column containing 50 g of silica gel (230-400 mesh) eluting with 5% acetone in methylene chloride (v/v) to give 0.035 g of the title compound as a white crystalline solid, mp 111°-115° C.

Workup

  1. temperaturewith cooling (ice bath)
  2. customThe bath was removed
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ice and water
  5. extractionextracted with ether
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationThe ether solution was filtered
  9. concentrationconcentrated in vacuo
  10. customto give a yellow oil, which
  11. temperatureAfter heating
  12. temperatureat reflux for 4 hours
  13. additioncontaining molecular sieves
  14. concentrationthe toluene solution was concentrated in vacuo

Sources & evidence

ORD record
ord-1cd0dbf567a74b19b9769459851ccaf7
Source dataset
uspto-grants-1987_03
Patent number
US04654363

Reaction notes

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