Hydrochloric Acid → 4-Oxocyclohexane-1-carbonitrile

HRID 844020Notes

Reaction equation

HRID 844020 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]#[N:12])[CH2:7][CH2:6]2)[O:4]CC1.Cl>O1CCCC1.C(OCC)(=O)C>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([C:11]#[N:12])[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 122356394-Oxocyclohexane-1-carbonitrileYield 50.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,4-Dioxa-spiro[4.5]decane-8-carbonitrile (2.0 grams, 12.8 mmole) and 2 N hydrochloric acid (21.0 grams, 42.0 mmole) in tetrahydrofuran (30 ml) at room temperature was stirred over night. The mixture was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered, and concentrated to an oil which was purified via flash chromatography on silica using 10% ethyl acetate/hexane as eluent to give an oil (0.800 g). MW 123.15.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil which
  5. customwas purified via flash chromatography on silica using 10% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-69969c4e2ca24327849718b9126b2250
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…