Sodium Hydroxide → HCID 86742961, compound

HRID 621732Notes

Reaction equation

HRID 621732 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-77a47b701cf4478eb79f8f8cd306b47d
Source dataset
uspto-grants-1989_04
Patent number
US04824959

Reaction notes

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