Water → Benzyl 3-cyclohexene-1-carboxylate

HRID 2104361Notes

Reaction equation

HRID 2104361 reaction equation
[CH:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C(N(CC)CC)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:17]([O:8][C:7]([CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)=[O:9])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 209033-Cyclohexene-1-carboxylic acid

Product 1

HCID 11020300Benzyl 3-cyclohexene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-3-Cyclohexene-1-carboxylic acid (50 g) was dissolved in N,N-dimethylformamide (550 mL), and to the solution were added triethylamine (170 mL) and benzyl bromide (61 mL) under ice cooling, followed by stirring at room temperature for 12 hours. Water was added to the resultant mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and was dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1), to thereby give the title compound (70.8 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-12d820dd49894850ace6a4aa9cf22e8c
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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