Methanol → HCID 69431017, compound

HRID 1269953Notes

Reaction equation

HRID 1269953 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([C:13]([OH:15])=[O:14])[CH2:8]1.[CH3:16]O>>[CH3:5][O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([C:13]([O:15][CH3:16])=[O:14])[CH2:8]1.[CH3:5][O:6][C@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([C:13]([O:15][CH3:16])=[O:14])[CH2:8]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 37022803-methoxycyclohexanecarboxylic acid

Product 2

HCID 69431017HCID 69431017, compoundYield 56%HCID 69431339HCID 69431339, compoundYield 29%

Procedure

Under a nitrogen atmosphere, thionyl chloride (11.3 g, 0.0948 mol) was slowly dropped into methanol (30 ml) at −5° C. over a period of 20 minutes. After 15 minutes, a solution of 3-methoxycyclohexylcarboxylic acid (5.0 g, 0.0316 mol, cis:trans=4:3) in methanol (30 ml) was added dropwise thereto over a period of 15 minutes. After 2.5 hours, the reaction solution was concentrated under reduced pressure, and the resulting residue was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution. The aqueous layer was re-extracted with ethyl acetate and then the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain methyl cis-3-methoxycyclohexane-carboxylate (3.0673 g, 56%) and methyl trans-3-methoxycyclohexanecarboxylate (1.5859 g, 29%).

Workup

  1. waitover a period of 15 minutes
  2. waitAfter 2.5 hours
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. additionthe resulting residue was diluted with ethyl acetate
  5. washwashed with a saturated aqueous sodium hydrogencarbonate solution
  6. extractionThe aqueous layer was re-extracted with ethyl acetate
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. customThe organic layer dried
  9. concentrationwas concentrated under reduced pressure
  10. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-baa30955bc5c47269cc3f5b63e972421
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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