Water → Benzyl 3-cyclohexene-1-carboxylate

HRID 459515Notes

Reaction equation

HRID 459515 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>[CH:1]1([C:7]([O:9][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]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 triethylamine (170 ml) and benzyl bromide (61 ml) were added under ice cooling to stir the mixture at room temperature for 12 hours. Water was added, extraction was conducted with ethyl acetate, and the resultant organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain the title compound (70.8 g) as a reddish brown oil.

Workup

  1. extractionextraction
  2. washthe resultant organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c027ec096df04d3f9040c174888e4cf0
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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