Hydrochloric Acid → 1,4-Dioxaspiro[4.5]decane-8-carboxylic acid

HRID 2047053Notes

Reaction equation

HRID 2047053 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]([O:13]CC)=[O:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C1COCC1.O.[OH-].[Li+].Cl>CO.O>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

Product 1

HCID 117453341,4-Dioxaspiro[4.5]decane-8-carboxylic acidYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (79.58 mmol, 17.05 g) is taken up in 300 mL 2:1 THF:H2O in 500 mL roundbottom flask. Lithium hydroxide monohydrate (120 mmol, 5.01 g) and 100 mL MeOH were added to this solution. The reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was acidified to pH 3 with 1N HCl(aq) and extracted with 100 mL DCM (×5). The combined organics were combined and then dried over Na2SO4, and the solvent was removed in vacuo to yield 1,4-dioxaspiro[4.5]decane-8-carboxylic acid (14.96 g, 100% yield) as white solid.

Workup

  1. extractionextracted with 100 mL DCM (×5)
  2. dry with materialdried over Na2SO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-708c35e529a149e1a114dfc07fa9a648
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…