Acetic Acid → Methyl cis-3-methoxymethoxycyclohexanecarboxylate

HRID 854639Notes

Reaction equation

HRID 854639 reaction equation
[CH:1]12[CH2:9][CH:5]([O:6][C:7]1=[O:8])[CH2:4][CH2:3][CH2:2]2.[CH3:10][O-:11].[Na+].[C:13](O)(=O)C.[CH3:17][OH:18]>>[CH3:10][O:11][CH2:17][O:18][C@@H:3]1[CH2:4][CH2:5][CH2:9][C@H:1]([C:7]([O:6][CH3:13])=[O:8])[CH2:2]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 2969126-Oxabicyclo(3.2.1)octan-7-oneHCID 10942334Sodium Methoxide

Product 1

HCID 69240434Methyl cis-3-methoxymethoxycyclohexanecarboxylate

Procedure

15 g of 6-oxabicyclo[3.2.1]octan-7-one are dissolved in 150 ml of methanol, 13 g of sodium methoxide are added and the mixture is stirred at room temperature for 2 h. 13.7 ml of glacial acetic acid are then added, and most of the solvent is distilled off under reduced pressure. The residue is taken up in water and extracted three times with in each case 100 ml of ethyl acetate. The organic phases are dried over MgSO4 and then concentrated under reduced pressure. This gives 18.8 g of the methyl ester as a colorless oil. This is dissolved in 150 ml of dichloromethane, 19.2 g of methoxymethyl chloride and 23.2 g of diisopropylethylamine are added and the mixture is stirred at room temperature for 15 h. 250 ml of saturated NH4Cl solution and 200 ml of water are added to the solution, and the organic phase is separated off. The aqueous phase is extracted with dichloromethane and the combined organic phases are dried over magnesium sulfate and concentrated. This gives 22.2 g of methyl cis-3-(methoxymethoxy)cyclohexanecarboxylate as a yellow oil. C10H18O4 (202), MS (ESI): 203 (MH+).

Workup

  1. distillationmost of the solvent is distilled off under reduced pressure
  2. extractionextracted three times with in each case 100 ml of ethyl acetate
  3. dry with materialThe organic phases are dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThis is dissolved in 150 ml of dichloromethane
  6. addition19.2 g of methoxymethyl chloride and 23.2 g of diisopropylethylamine are added
  7. stirringthe mixture is stirred at room temperature for 15 h
  8. addition250 ml of saturated NH4Cl solution and 200 ml of water are added to the solution
  9. customthe organic phase is separated off
  10. extractionThe aqueous phase is extracted with dichloromethane
  11. dry with materialthe combined organic phases are dried over magnesium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-ec193beac84840948fa0df4bf417a020
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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