Citric Acid → 8-Ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylic acid

HRID 1969896Notes

Reaction equation

HRID 1969896 reaction equation
[CH2:1]([CH:3]1[CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH:4]1[C:12]([O:14]CC)=[O:13])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH2:1]([CH:3]1[CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][CH:4]1[C:12]([OH:14])=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 58557462Ethyl 8-ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylate

Product 1

HCID 585573038-Ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with ethyl 8-ethyl-1,4-dioxaspiro[4.4]nonane-7-carboxylate (0.32 g, 1.4 mmol) and aqueous sodium hydroxide (1 N, 14.0 mL, 14.0 mmol). The solution was stirred overnight at rt. To the solution was added DCM (30 mL) followed by the addition of 20% aqueous citric acid (about 20 mL) to reach pH of about 2. The layers were separated and the aqueous solution was extracted with DCM (2×30 mL) and DCM/EtOAc (1:1, 30 mL). The combined extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 8-ethyl-1,4-dioxaspiro[4.4]nonane-7-carboxylic acid as a clear, colorless oil (0.27 g, 96%): LC/MS (Table 1, Method c) Rt=1.20 min; MS m/z: 201 (M+H)+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous solution was extracted with DCM (2×30 mL) and DCM/EtOAc (1:1, 30 mL)
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-14ee3734f31949289f06eae7c604274f
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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