Sulfuric Acid → 4-Prop-2-ynylcyclohexanecarboxylic acid

HRID 1977095Notes

Reaction equation

HRID 1977095 reaction equation
S(=O)(=O)(O)[OH:2].[CH2:6]([CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]1)[C:7]#[CH:8]>CC(C)=O.CCOCC.[O-2].[O-2].[O-2].[Cr+6]>[CH2:6]([CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:2])=[O:16])[CH2:11][CH2:10]1)[C:7]#[CH:8]

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 10796940(4-Prop-2-ynylcyclohexyl)methanol

Product 1

HCID 107971444-Prop-2-ynylcyclohexanecarboxylic acidYield 75%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of chromium trioxide (1.1 g, 11 mmol) in 1.5 M sulfuric acid (40 mL, 27 mmol) was maintained at 0° C. while 5.3 (0.46 g, 3 mmol) in 80 mL of acetone was added over 2 hours. The reaction was then stirred for an additional 2 hours at room temperature. The reaction mixture was diluted with ether (200 mL) and extracted 2 times with water. The organics were dried with sodium sulfate. The solvent was removed under reduced pressure and the product was purified by chromatography on silica gel column eluting with acetone-dichloromethane (70:30) to give 5.4 (75%). 1H NMR (300 MHz, CDCl3) δ 2.24 (dt, J=3.66, 12.1 Hz, 1 H), 2.10 (dd, J=2.7, 6.5 Hz, 2 H), 2.04-1.89 (m, 5 H), 1.76 (d, J=2.3 Hz, 1 H), 1.43 (dq, J=3.28, 13.1 Hz, 2 H), 1.03 (dq, J=3.28, 13.1 Hz, 2 H). 13C NMR (300 MHz, CDCl3) δ 183.2, 83.3, 69.9, 43.4, 36.7, 31.8, 28.9, 26.3.

Workup

  1. additionwas added over 2 hours
  2. extractionextracted 2 times with water
  3. dry with materialThe organics were dried with sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by chromatography on silica gel column
  6. washeluting with acetone-dichloromethane (70:30)

Sources & evidence

ORD record
ord-ced87d7223e543d392dc40fd8a1eec0d
Source dataset
uspto-grants-2001_05
Patent number
US06232297B1

Reaction notes

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