Methanol → Methyl cyclooctanecarboxylate

HRID 588672Notes

Reaction equation

HRID 588672 reaction equation
[CH:1]1([CH:9]=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.OOS([O-])=O.[K+].[CH3:17][OH:18]>>[CH:1]1([C:9]([O:18][CH3:17])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 81190CyclooctanecarbaldehydeHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 77313Methyl cyclooctanecarboxylate

Procedure

To a solution of cyclooctanecarbaldehyde (5.0 g) in methanol (300 mL) was added Oxone (22 g). The mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under vacuum and the residue was diluted with ethyl acetate (300 mL) and washed with 1N aqueous HCl, water, and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionthe residue was diluted with ethyl acetate (300 mL)
  3. washwashed with 1N aqueous HCl, water, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5306a49dc82942aca8da0663f28ab36d
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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