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

HRID 1913226Notes

Reaction equation

HRID 1913226 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 (Int-5a, 79.58 mmol, 17.05 g) was taken up in 300 mL 2:1 THF:H2O in 500 mL round-bottom flask. To this solution was added lithium hydroxide monohydrate (120 mmol, 5.01 g). To this was added 100 mL MeOH. The reaction 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 (x5). The combined organics were then dried over Na2SO4 and the solvents were removed in vacuo to yield 1,4-dioxaspiro[4.5]decane-8-carboxylic acid (Int-5b) (14.96 g, 100% yield) as a white solid.

Workup

  1. extractionextracted with 100 mL DCM (x5)
  2. dry with materialThe combined organics were then dried over Na2SO4
  3. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-d43b24530c9643f5b75d859194caf9de
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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