Cyclohexylpropionyl chloride → 107974-71-0

HRID 358931Notes

Reaction equation

HRID 358931 reaction equation
C([Li])CCC.CC(C)([O-])C.[Li+].[C:12]([Li])([CH3:15])([CH3:14])[CH3:13].[CH:17]1([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>O1CCCC1.C(O)CCC>[CH3:13][C:12]([CH3:15])([C:25]([CH2:24][CH2:23][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:26])[CH3:14]

Participants

7

Reactant 4

HCID 2734098Cyclohexylpropionyl chlorideHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 178418306HCID 178418306, compoundHCID 178418339Butyllithium

Product 1

HCID 43370345107974-71-0

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Stage 1 of the preparation was carried out under an argon atmosphere. To a stirred solution of t butyl alcohol (4.92 g) in tetrahydrofuran (20 ml) at -30° C. was added dropwise n-butyl lithium (41.8 ml of 1.6 molar solution). The resultant lithium t-butoxide solution was allowed to warm to 0° C. and was added to a stirred solution of cuprous iodide (12.65 g) in tetrahydrofuran (50 ml). After about 15 minutes, the grey cuprous iodide was replaced by a beige solid, and the reaction mixture turned brown. The reaction mixture was then cooled to -70° C. and t-butyl lithium (34.0 ml of 1.9 molar solution) was added dropwise. A cooled (-40° C.) solution of 3-cyclohexyl propionic acid chloride (10 .0 g) in tetrahydrofuran (20 ml) was added rapidly. After 11/2 hours, the reaction was quenched by the addition of methanol (30 ml) and the reaction mixture was allowed to stand overnight at room temperature. The mixture was then poured into saturated ammonium chloride (200 ml) and insolubles were filtered off. The aqueous layer was extracted with ether (300 ml) and the extract was washed with 1% sodium thiosulphate solution (200 ml) and then dried over magnesium sulphate in the presence of charcoal. Concentration yielded an amber oil which was distilled to give a colourless liquid (5.56 g) which turned yellow on standing.

Workup

  1. temperatureThe reaction mixture was then cooled to -70° C.
  2. additionwas added rapidly
  3. customAfter 11/2 hours, the reaction was quenched by the addition of methanol (30 ml)
  4. waitto stand overnight at room temperature
  5. additionThe mixture was then poured into saturated ammonium chloride (200 ml) and insolubles
  6. filtrationwere filtered off
  7. extractionThe aqueous layer was extracted with ether (300 ml)
  8. washthe extract was washed with 1% sodium thiosulphate solution (200 ml)
  9. dry with materialdried over magnesium sulphate in the presence of charcoal
  10. concentrationConcentration
  11. customyielded an amber oil which
  12. distillationwas distilled

Sources & evidence

ORD record
ord-4201ecc19a9d4333b43fd035496451cb
Source dataset
uspto-grants-1991_03
Patent number
US04999043

Reaction notes

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