Pyridine → 3,3-Diphenylpropanol

HRID 267818Notes

Reaction equation

HRID 267818 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH2:9][CH3:10])O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:19]C(=O)C)C.[N-]=C=O.N1C=CC=CC=1>CCOCC>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:10][OH:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2261491,1-Diphenylpropan-1-olHCID 19995369Isocyanate acetic acid ethyl ester

Product 1

HCID 299083,3-Diphenylpropanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.2 G of diphenyl-ethyl-carbinol, 1.9 g of isocyanate acetic acid ethyl ester and 1.6 ml of pyridine are heated at 50° C for 72 hours. The solution is diluted with 50 ml of ether, washed several times at 0° C with 0.1-molar citric acid solution and water, dried over sodium sulfate, and completely evaporated under reduced pressure. After elimination of 2.3 g of diphenylethylcarbinol by means of petroleum ether, 1,1-diphenyl-propyloxycarbonyl-glycine-ethyl ester is obtained in the form of an oil; Rf = 0.2 in the thin-layer chromatogram in chloroform.

Workup

  1. washwashed several times at 0° C with 0.1-molar citric acid solution and water
  2. dry with materialdried over sodium sulfate
  3. customcompletely evaporated under reduced pressure

Sources & evidence

ORD record
ord-76361e8d5e2c411f9b26ed2bf97e0db9
Source dataset
uspto-grants-1976_03
Patent number
US03944590

Reaction notes

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