Ethyl Acetate → 2-Cyanomethyl-3-hexadecyloxypropyl benzoate

HRID 847013Notes

Reaction equation

HRID 847013 reaction equation
[C:1]([O:9][CH2:10][CH:11]([CH2:30]Br)[CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:32]#[N:33].[Na+].C(OCC)(=O)C>CS(C)=O>[C:1]([O:9][CH2:10][CH:11]([CH2:30][C:32]#[N:33])[CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 537978482-Bromomethyl-3-hexadecyloxypropanol benzoate

Product 1

HCID 545411872-Cyanomethyl-3-hexadecyloxypropyl benzoateYield 100.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 13.845 g (27.9 mM) of 2-bromomethyl-3-n-hexadecyloxypropyl benzoate n3 and 1.439 g (27.9 mM) of sodium cyanide (95% purity) in 150 ml of dimethylsulfoxide is heated at 90° C. for 1 hour. The product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with water (four times) and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated to obtain 12.42 g of the crude product of the titled compound n3'.

Workup

  1. washThe ethyl acetate layer is washed with water (four times) and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-bb0dbdf8d9b4421a8c09d5ab7bc707d4
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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