Benzyl Bromide → HCID 178525075, compound

HRID 1189474Notes

Reaction equation

HRID 1189474 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[OH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:10])[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178525728HCID 178525728, compound

Product 1

HCID 178525075HCID 178525075, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.0 g of trans-4-(hydroxymethyl)cyclohexanecarboxylic acid, 20 mL of N,N-dimethylformamide, 1.32 g of potassium carbonate, and 0.24 g of tetrabutylammonium iodide was added dropwise 0.83 mL of benzyl bromide at room temperature, followed by stirring overnight. The reaction liquid was filtered and then the filtrate was concentrated. To the residue were added ethyl acetate and water, and the aqueous layer was separated. The organic layer was washed with water, a saturated aqueous ammonium chloride solution, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine in this order, and dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain 1.70 g of benzyl trans-4-(hydroxymethyl)cyclohexane carboxylate.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. additionTo the residue were added ethyl acetate and water
  5. customthe aqueous layer was separated
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous ammonium chloride solution, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine in this order, and dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-859def6de1ae4f24915368bc3b621d47
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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