Hydrochloric Acid → HCID 86731478, compound

HRID 1773026Notes

Reaction equation

HRID 1773026 reaction equation
[CH2:1]([O:3][C:4]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6][CH2:5]1)[CH3:2].Cl>O1CCOCC1.O>[CH2:1]([O:3][C:4]1([C:14]([OH:16])=[O:15])[CH2:5][CH2:6][C:7](=[O:8])[CH2:12][CH2:13]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86731479HCID 86731479, compound

Product 1

HCID 86731478HCID 86731478, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the 8-ethoxy-1,4-dioxaspiro[4.5]decane-8-carboxylic acid in 1,4-dioxane (20 mL) was added HCl (6N) (7.53 mL, 45.2 mmol) and the mixture was stirred at rt for 16 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (3×40 mL). The organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 1-ethoxy-4-oxocyclohexanecarboxylic acid (0.777 g, 4.17 mmol, 65% yield over 2 steps) as a red oil. 1H NMR (500 MHz, CHLOROFORM-d) δ=3.59 (q, J=7.0 Hz, 2H), 2.66-2.55 (m, 2H), 2.42-2.33 (m, 4H), 2.24-2.15 (m, 2H), 1.31 (t, J=6.9 Hz, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. washThe organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf44080aca6f40d69d3b3453f0c86627
Source dataset
uspto-grants-2016_02
Patent number
US09249180B2

Reaction notes

Loading…