Sodium Carbonate → Mellein

HRID 594923Notes

Reaction equation

HRID 594923 reaction equation
CCCCCCCCCCCCCCCCCCN[C:20]([CH2:22][CH2:23][C:24]1[CH:29]=[C:28](C(C)(C)C)[C:27](O)=[C:26](C(C)(C)C)[CH:25]=1)=O.[O-:39][Mn](=O)(=O)=O.[K+].[C:45]([O-])([O-:47])=[O:46].[Na+].[Na+]>CC(O)=O.O>[CH3:20][CH:22]1[O:47][C:45](=[O:46])[C:29]2[C:28]([OH:39])=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:23]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 516875Potassium PermanganateHCID 197363073,5-Bis(1,1-dimethylethyl)-4-hydroxy-N-octadecylbenzenepropanamide

Product 1

HCID 28516Mellein

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of AO-1 (16.5 g, 83.0 mmol) in AcOH (150 mL) kept below 10° C. is added a solution of KMnO4 (14.5 g, 92.0 mmol) in H2O (150 mL) dropwise. The reaction mixture is stirred for 30 min. The mixture is diluted with water, basified by addition of saturated aq Na2CO3 and extracted with EtOAc. The solution is concentrated and the residue is purified by SFC to yield AO-2.

Workup

  1. customkept below 10° C.
  2. extractionextracted with EtOAc
  3. concentrationThe solution is concentrated
  4. customthe residue is purified by SFC

Sources & evidence

ORD record
ord-d400661187fc4bccad7895e0d676b0bc
Source dataset
uspto-grants-2016_01
Patent number
US09242989B2

Reaction notes

Loading…