Methanol → HCID 178501284, compound

HRID 1873591Notes

Reaction equation

HRID 1873591 reaction equation
S(=O)(=O)(O)O.[OH:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1.[CH3:16]O>>[OH:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178525779HCID 178525779, compound

Product 1

HCID 178501284HCID 178501284, compound

Procedure

2.95 liters of methanol and 9.7 ml of conc. sulfuric acid are initially charged, and 175.0 g (1.21 mol) of cis-4-hydroxycyclohexanecarboxylic acid are added a little at a time at RT. The mixture is stirred at RT for 16 h. Almost all of the solvent is then removed on a rotary evaporator and the residue is taken up in 2 liters of a 1:1 mixture of saturated aqueous sodium bicarbonate solution and ethyl acetate. The phases are separated, and the organic phase is washed with 1 liter of 10% strength aqueous ammonium chloride solution and then dried over magnesium sulfate. After removal of the solvent on a rotary evaporator the residue is purified chromatographically on silica gel 60 (mobile phase: gradient ethyl acetate/petroleum ether 3:7→1:1).

Workup

  1. customAlmost all of the solvent is then removed on a rotary evaporator
  2. additionthe residue is taken up in 2 liters of a 1:1 mixture of saturated aqueous sodium bicarbonate solution and ethyl acetate
  3. customThe phases are separated
  4. washthe organic phase is washed with 1 liter of 10% strength aqueous ammonium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent
  7. customon a rotary evaporator the residue
  8. customis purified chromatographically on silica gel 60 (mobile phase: gradient ethyl acetate/petroleum ether 3:7→1:1)

Sources & evidence

ORD record
ord-8d251a0e5c7a4ce1b797630ceb9604de
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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