1-Bromopropane → Propyl cyclohexanecarboxylate

HRID 656696Notes

Reaction equation

HRID 656696 reaction equation
[Na+].[CH:2]1([C:8]([O-:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Br[CH2:12][CH2:13][CH3:14]>C1COCC1>[CH2:12]([O:9][C:8]([CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:10])[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 78401-BromopropaneHCID 23673627Sodium cyclohexanecarboxylate

Product 1

HCID 81222Propyl cyclohexanecarboxylateYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To cyclohexanecarboxylic acid sodium salt (5.0 g, 33.3 mmol) in THF (80 mL) tetrabutylammonium bromide (1.074 g, 3.33 mmol) and 1-bromopropane (4.545 g, 49.95 mmol) in THF (120 mL) were added. The mixture was stirred 72 h at 50° C., cooled to room temperature and filtered. The precipitate was washed with THF. The filtrate was concentrated and the residue diluted with TBME. The solution was washed with water and the aqueous phases were re-extracted with TBME. The organic phases were combined, dried over sodium sulfate and evaporated to afford 4.2 g (74%) cyclohexanecarboxylic acid n-propyl ester as a liquid, GC purity 99% (area). 1H-NMR (CDCl3, 400 MHz): ppm 0.94 (t, 3H), 1.15-1.36 (m, 3H), 1.38-1.50 (m, 2H), 1.55-1.81 (m, 5H), 1.85-1.92 (m, 2H), 2.23-2.32 (m, 1H), 4.02 (q, 2H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe precipitate was washed with THF
  4. concentrationThe filtrate was concentrated
  5. additionthe residue diluted with TBME
  6. washThe solution was washed with water
  7. extractionthe aqueous phases were re-extracted with TBME
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-e4744d0268e7405e805e836310f2ce28
Source dataset
uspto-grants-2011_12
Patent number
US08071803B2

Reaction notes

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