Cyclohexanecarboxylic acid → HCID 19205727, compound

HRID 251517Notes

Reaction equation

HRID 251517 reaction equation
[CH:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Li+:12]>CO>[Li+:12].[CH:1]1([C:7]([O-:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Procedure

Under stirring, a solution of cyclohexanecarboxylic acid (10.0 g, 78 mmol) in MeOH (30 mL) was added dropwise over 30 min to 1 M lithium methoxide in MeOH (78 mL, 78 mmol) at 5-10° C. The cooling bath was removed and after 4 h at room temperature, heptane (75 mL) was added slowly. Most of the MeOH was removed at a rotary evaporator. Heptane (100 mL) was added to the thick white suspension which was stirred 2 h at 0° C. The suspension was filtered and the filter cake was washed with heptane and dried in vacuo (<1 mbar) to afford 10.5 g (100%) cyclohexanecarboxylic acid lithium salt. Anal. Calcd for C7H11LiO2 C, 62.70; H, 8.27. Found: C, 62.03; H, 8.11; H2O, 0.67.

Workup

  1. customThe cooling bath was removed and after 4 h at room temperature
  2. additionheptane (75 mL) was added slowly
  3. customMost of the MeOH was removed at a rotary evaporator
  4. additionHeptane (100 mL) was added to the thick white suspension which
  5. stirringwas stirred 2 h at 0° C
  6. filtrationThe suspension was filtered
  7. washthe filter cake was washed with heptane
  8. customdried in vacuo (<1 mbar)

Sources & evidence

ORD record
ord-f94055c7039542c09dac4dd54137f456
Source dataset
uspto-grants-2011_01
Patent number
US07863474B2

Reaction notes

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