Acetic Acid → HCID 50923868, compound

HRID 1170817Notes

Reaction equation

HRID 1170817 reaction equation
[C:1]([O:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(O)(=[O:17])C>>[C:1]([O:7][CH:8]1[CH2:13][CH2:12][C:11]([OH:17])([CH3:14])[CH2:10][CH2:9]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 66870880HCID 66870880, compound

Product 1

HCID 50923868HCID 50923868, compound

Procedure

FIG. 2 represents chemical structures, reaction schemes and reaction yields for an example of an oxidation of the substrate 4-methylcyclohexyl pivalate in the presence of two different complexes. Experimental details are provided in Examples 3 and 4. Reaction of the substrate with complex 4 in the presence of acetic acid (AcOH) yielded 38% (by GC) of the mono-oxidized product 4-hydroxy-4-methylcyclohexyl pivalate (entry 4). This yield was amplified by using a three-fold reagent addition procedure, in which each addition of the complex included 5 mol % complex 4 and 0.5 equivalent AcOH, and each addition of oxidant included 1.2 equivalents H2O2. The three-fold reagent addition procedure was carried out over a period of 30 minutes, providing diastereomerically pure hydroxylated product 2 in 51% isolated yield (entry 5).

Workup

  1. customchemical structures, reaction schemes and reaction
  2. customExperimental details are provided in Examples 3 and 4

Sources & evidence

ORD record
ord-1d71a6b75d5c4dcb85efb1c63e10ed4b
Source dataset
uspto-grants-2010_11
Patent number
US07829342B2

Reaction notes

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