4-Hydroxybenzaldehyde → 4-(5-Methyl-2-phenyl-4-oxazolyl)methoxybenzaldehyde

HRID 4410

Reaction equation

HRID 4410 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:8][C:7]1[O:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 107561164-(5-Methyl-2-phenyl-4-oxazolyl)methoxybenzaldehydeYield 100.1%

Conditions

Temperature
110 °C

Procedure

A mixture of 4-chloromethyl-5-methyl-2-phenyloxazole (3.12 g), 4-hydroxybenzaldehyde (1.83 g), potassium carbonate (2.28 g) and dimethylformaide (40 ml) was stirred under heating at 110° C. for 1 hour. The reaction solution was poured into ice-cold water, and the crystals which separated out were collected by filtration to give 4-(5-methyl-2-phenyl-4-oxazolyl)methoxybenzaldehyde (4.40 g, 99.8%). Recrystallization from ether-hexane yielded colorless prisms, m.p. 112°-113° C. Elemental analysis for C18H15NO3 ; Calcd.: C, 73.71; H, 5.15; N, 4.87. Found: C, 73.87; H, 5.26; N, 4.81.

Workup

  1. additionThe reaction solution was poured into ice-cold water
  2. customthe crystals which separated out
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-87fabac48c9340eaa4907ce30b7c5b7e
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

Loading…