4,5-Dihydro-2,4,4-trimethyloxazole → 5-(2'-Chloro-5'-nitrophenyl)-4-methyl-2,4-pentadienoic acid

HRID 893189

Reaction equation

HRID 893189 reaction equation
[OH:1]S([O-])=O.[Na+].[Cl:6][C:7]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:8]=1[CH:9]=[C:10]([CH3:13])[CH:11]=O.CC1[O:23][CH2:24][C:25](C)(C)N=1>C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:8]=1[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:25][C:24]([OH:1])=[O:23]

Participants

5

Reactant 3

HCID 744964,5-Dihydro-2,4,4-trimethyloxazoleHCID 23665763Sodium BisulfiteHCID 544427022-Chloro-5-nitro-alpha-methylcinnamaldehyde

Product 1

HCID 539242065-(2'-Chloro-5'-nitrophenyl)-4-methyl-2,4-pentadienoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

0.3 g of a 40 percent strength NaHSO3 solution is added to a mixture of 9 g of 2-chloro-5-nitro-α-methylcinnamaldehyde and 10.4 g of 2,4,4-trimethyloxazoline in 50 ml of toluene, and the mixture is refluxed for 10 hours. It is evaporated down, and 10 ml of water and 10 ml of concentrated HCl are added to the crude product of the structure ##STR23## Heating at 100° C. for 7 hours results in cleavage of the oxazoline ring. The crude product is filtered off under suction, washed with water and dried. Yield: 7.1 g (66%), mp. 178°-185° C.

Workup

  1. temperaturethe mixture is refluxed for 10 hours
  2. customIt is evaporated down
  3. addition10 ml of water and 10 ml of concentrated HCl are added to the crude product of the structure
  4. customresults in cleavage of the oxazoline ring
  5. filtrationThe crude product is filtered off under suction
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-1095fe112043484d9a4aa57594264db2
Source dataset
uspto-grants-1992_06
Patent number
US05123955

Linked notes

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