Sodium Hydroxide → HCID 86742961, compound

HRID 1195399Notes

Reaction equation

HRID 1195399 reaction equation
[CH:1]([CH:6]1[O:11][C:10]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[O:9][CH:8]([CH2:17][C:18]([O:20]C)=[O:19])[CH2:7]1)=[CH:2][CH:3]=[CH:4][CH3:5].[OH-].[Na+]>CO>[CH:1]([C@H:6]1[O:11][C:10]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[O:9][C@@H:8]([CH2:17][C:18]([OH:20])=[O:19])[CH2:7]1)=[CH:2][CH:3]=[CH:4][CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53899221HCID 53899221, compound

Product 1

HCID 86742961HCID 86742961, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(1,3-pentadienyl)-1,5-dioxaspiro[5.5]undecane-2-acetate (3.5 g, 12.4 mmol) was heated to reflux in a solution of 1N NaOH (13 mL) and methanol (26 mL). Methanol was removed under reduced pressure and the remaining aqueous solution was acidified with 1N HCl and extracted with diethyl ether. The organic layer was dried (Na2SO4) and concentrated. The residual solid was recrystallized from ethyl acetate/hexane to afford 2.0 g (55.9%) of the title compound as a colorless solid; m.p.=144°-146.5° C.

Workup

  1. customMethanol was removed under reduced pressure
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residual solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bbd18976e7d74f86b8a52c3a9a92ab4e
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

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