2-Chlorobenzaldehyde → HCID 53929795, compound

HRID 2082919Notes

Reaction equation

HRID 2082919 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].O[C:11]1[CH:12]=[C:13]([CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:14]=[CH:15][C:16]=1[NH2:17]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]1[O:5][C:11]2[CH:12]=[C:13]([CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:14]=[CH:15][C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 69962-ChlorobenzaldehydeHCID 12370790HCID 12370790, compound

Product 1

HCID 53929795HCID 53929795, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of o-chlorobenzaldehyde (4.3 g.) and ethyl 2-(3-hydroxy-4-aminophenyl)propionate (6 g.) in toluene (100 ml.) was heated, using a Dean and Stark apparatus to collect the water formed. After 30 minutes the solution was evaporated to dryness. The residue was dissolved in acetic acid (100 ml.), lead tetracetate (15 g.) was added and the solution was heated on a steam bath for 1 hour. The solution was poured into ice/water and extracted with ether to give the oil, ethyl 2-(2-o-chlorophenyl-6-benzoxazolyl)propionate, a sample of which gave a satisfactory micro-analysis.

Workup

  1. customto collect the water
  2. customformed
  3. customAfter 30 minutes the solution was evaporated to dryness
  4. dissolutionThe residue was dissolved in acetic acid (100 ml.)
  5. additionlead tetracetate (15 g.) was added
  6. temperaturethe solution was heated on a steam bath for 1 hour
  7. additionThe solution was poured into ice/water
  8. extractionextracted with ether

Sources & evidence

ORD record
ord-e11c81b25e19471ea439ffb8c16ccf99
Source dataset
uspto-grants-1978_04
Patent number
USRE029608

Reaction notes

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