Methanol → Methyl cycloheptanecarboxylate

HRID 1430268Notes

Reaction equation

HRID 1430268 reaction equation
[CH:1]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.OS(O)(=O)=O.[CH3:16]O>>[CH:1]1([C:8]([O:10][CH3:16])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 15091Cycloheptanecarboxylic acid

Product 1

HCID 543492Methyl cycloheptanecarboxylate

Procedure

To a solution of 25.0 g cycloheptanecarboxylic acid in methanol (300 mL) was added concentrated H2SO4 (0.5 g) and the mixture was stirred at reflux overnight. The reaction mixture was concentrated under vacuum and the residue was diluted with ethyl ether (500 mL). The mixture was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionthe residue was diluted with ethyl ether (500 mL)
  4. washThe mixture was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2691980ff03941ccbf4c3876102a151c
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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