Lithium Hydroxide → 1,4-Dioxaspiro[4.5]decane-8-carboxylic acid

HRID 1913331Notes

Reaction equation

HRID 1913331 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.[Li+].[OH-]>CO>[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

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

Product 1

HCID 117453341,4-Dioxaspiro[4.5]decane-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.0 g (14 mmol) of the ethyl ester precursor, ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate, were dissolved in 5 ml of methanol and admixed at RT slowly with 28 ml (2 eq.) of 1 M LiOH solution. The mixture was stirred overnight; HPLC-MS indicated complete reaction. Methanol was distilled off under reduced pressure and the residue was acidified cautiously with 1 ml of HCl such that no acid excess was present. The mixture was extracted with ethyl acetate, and the ethyl acetate phase was dried over sodium sulfate and then concentrated by evaporation under reduced pressure. Yield: 2.25 g, 86% of theory.

Workup

  1. customreaction
  2. distillationMethanol was distilled off under reduced pressure
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe ethyl acetate phase was dried over sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-8227287cd1af4969bc86b4ecd06e84bc
Source dataset
uspto-grants-2013_12
Patent number
US08609681B2

Reaction notes

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