Sodium Carbonate → Oxypinocamphone

HRID 1721531Notes

Reaction equation

HRID 1721531 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=[O:2].[C:13]12(O)[CH2:21][CH:17]([C:18]1([CH3:20])[CH3:19])[CH2:16][CH2:15][C:14]2([OH:23])[CH3:22].C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O.C1COCC1>[OH:23][C:14]1([CH3:22])[C:15](=[O:2])[CH2:16][CH:17]2[CH2:21][CH:13]1[C:18]2([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1087942-Iodoxybenzoic acidHCID 219250472,6,6-Trimethylbicyclo[3.1.1]heptane-1,2-diol

Product 1

HCID 112005OxypinocamphoneYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

o-Iodoxybenzoic acid I (420 mg; 1.5 mmol) was added under stirring in one portion to a solution of pinanediol (170 mg; 1 mmol) in DMSO (3.4 ml) and THF (2.9 ml) at 0° C. After 3 h the reaction was poured in 20 ml of a solution of Na2CO3 (10%) and extracted with diethyl ether (3×10 ml). The combined organic layers were dried over sodium sulfate. The organic solvent was distilled under vacuum. The residue was purified by chromatography (SiO2, dichloromethane) to give after trituration with n-hexane, 145 mg (86%) of 2-hydroxy-pinanone, mp 30°-32° C.

Workup

  1. extractionextracted with diethyl ether (3×10 ml)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. distillationThe organic solvent was distilled under vacuum
  4. customThe residue was purified by chromatography (SiO2, dichloromethane)

Sources & evidence

ORD record
ord-ba6b33f887c34d88886a99a5f7575c4c
Source dataset
uspto-grants-1996_04
Patent number
US05510538

Reaction notes

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