Hydrochloric Acid → 2,2,5-Trimethylcyclopentanone

HRID 530237Notes

Reaction equation

HRID 530237 reaction equation
[CH3:1][C:2]1([C:10]([O-])=O)[CH2:6][CH2:5][C:4](C)([CH3:7])[C:3]1=[O:9].[K+].Cl>CO.O>[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][CH:4]([CH3:7])[C:3]1=[O:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 117720216HCID 117720216, compound

Product 1

HCID 1382972,2,5-Trimethylcyclopentanone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of the product of Example 8c in methanol and water (7.4 g, ˜35.7 mmol) was acidified with concentrated hydrochloric acid to pH=1 and then heated to reflux for 1 hour. The reaction mixture was cooled and then diluted with water (70 mL) and the organics were extracted with diethyl ether (80 mL×4). The combined organic phase was washed with brine (160 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as a light yellow liquid contaminated with some solvent (4.93 g, Purity: ˜85%). 1H NMR (400 MHz, CDCl3) δ 2.26-2.09 (m, 2H), 1.85-1.79 (m, 1H), 1.72-1.64 (m, 1H), 1.54-1.45 (m, 1H), 1.12 (d, J=6.8 Hz, 3H), 1.08 (s, 3H), 0.98 (s, 3H) ppm.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. extractionthe organics were extracted with diethyl ether (80 mL×4)
  5. washThe combined organic phase was washed with brine (160 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76d24daa8e194a918e33896820a1149d
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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