Potassium Hydroxide → 6-Oxaspiro(2.5)octane-1-carboxylic acid

HRID 656246Notes

Reaction equation

HRID 656246 reaction equation
[CH:1]1([C:9]([O:11]CC)=[O:10])[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1.[OH-].[K+]>C(O)C.O>[CH:1]1([C:9]([OH:11])=[O:10])[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57429837Ethyl 6-oxaspiro[2.5]octane-1-carboxylate

Product 1

HCID 532757266-Oxaspiro(2.5)octane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 120.50 g of ethyl 6-oxaspiro[2.5]-octane-1-carboxylate in 700 ml of ethanol/water 3.5:1 is mixed with 55.20 g of potassium hydroxide. The reaction mixture is heated at 60° C. for 4 hours, the ethanol is distilled off and the aqueous residue is diluted with water and extracted with tert-butyl methyl ether. The aqueous phase is adjusted to pH 2 with 4M hydrochloric acid and extracted with tert-butyl methyl ether. The combined organic extracts are washed with brine, dried with sodium sulphate and evaporated. The title compound is obtained as a yellowish oil and is employed without further purification for the next stage. Rt=2.13 (Gradient I).

Workup

  1. distillationthe ethanol is distilled off
  2. additionthe aqueous residue is diluted with water
  3. extractionextracted with tert-butyl methyl ether
  4. extractionextracted with tert-butyl methyl ether
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried with sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-bcef4d5cff6e4d6085318c1639b0946e
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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