Isopropanol → 2-Methoxycyclohexanone

HRID 1167409Notes

Reaction equation

HRID 1167409 reaction equation
CC[C@@H]1[C@@H]2C[C@@H]([C@H](O)C3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)N=CC=3)N(CC2)C1.[OH-:23].[Na+].[CH:25]([OH:28])(C)C>C[N+](C)(C)C.[Cl-]>[CH3:25][O:28][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][C:21]1=[O:23]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 6914728Dihydrocinchonidine

Product 1

HCID 1109982-Methoxycyclohexanone

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Procedure

Example 1 is repeated, except that isopropanol is used as solvent, 10 mg of hydrocinchonidine are used as modifier and 100 mg of catalyst are used. In addition, 800 mg of Amberlite IRA-900 (strongly basic anion exchanger, activated using NaOH) are added. The yield is 0.36 g of product of 95% purity containing 5% solvent (44%).

Workup

  1. additionare added

Sources & evidence

ORD record
ord-61d0b03ba9bd4e2c877b06e3ba56c223
Source dataset
uspto-grants-2003_09
Patent number
US06617475B2

Reaction notes

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