Mandelic Acid → 2-[2-(alpha-Hydroxybenzyl)-5-benzoxazolyl]propionitrile

HRID 2398757Notes

Reaction equation

HRID 2398757 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:5]([CH3:8])[C:6]#[N:7].[C:13](O)(=O)[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:15]>C1(C)C(C)=CC=CC=1>[OH:15][CH:14]([C:13]1[O:12][C:11]2[CH:10]=[CH:9][C:4]([CH:5]([CH3:8])[C:6]#[N:7])=[CH:3][C:2]=2[N:1]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1292Mandelic AcidHCID 122026362-(3-Amino-4-hydroxyphenyl)propanenitrile

Product 1

HCID 203195792-[2-(alpha-Hydroxybenzyl)-5-benzoxazolyl]propionitrile

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 3-amino-4-hydroxyhydratroponitrile (10 g.), mandelic acid (14 g.) and xylene (300 ml.) was heated using a Dean and Stark apparatus for 24 hours. The solution was filtered, evaporated to dryness and the residue dissolved in chloroform. The solution was washed with acid and base, dried over sodium carbonate and was eluted down a silica gel column with ether to give 2-[2-(α-hydroxybenzyl)-5-benzoxazolyl] propionitrile, the structure of which was confirmed by n.m.r. spectroscopy.

Workup

  1. temperaturewas heated
  2. customfor 24 hours
  3. filtrationThe solution was filtered
  4. customevaporated to dryness
  5. dissolutionthe residue dissolved in chloroform
  6. washThe solution was washed with acid and base
  7. dry with materialdried over sodium carbonate
  8. washwas eluted down a silica gel column with ether

Sources & evidence

ORD record
ord-af9224f88f6a4b7eb19d657410686bd0
Source dataset
uspto-grants-1977_05
Patent number
US04025637

Reaction notes

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