Sulfuric Acid → Coumarin

HRID 1637399Notes

Reaction equation

HRID 1637399 reaction equation
S(=O)(=O)(O)O.[C:6]1(N)[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1N.C([O:16][C:17](=[O:21])[CH2:18][C:19]#N)C.C(C1C=CC(O)=CC=1N(OCCC)OCCC)=O>>[O:21]1[C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:19]=[CH:18][C:17]1=[O:16]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 7243O-Phenylenediamine2×HCID 7764Ethyl cyanoacetateHCID 19349303HCID 19349303, compound

Product 1

HCID 323Coumarin

Conditions

Temperature
92.5 °C

Procedure

100 parts of 50% sulfuric acid were charged to a reactor vessel to which 10.8 parts of o-phenylenediamine and 11.4 parts of ethylcyanoacetate were then subsequently added. This mixture was heated to a reflux until all of the o-phenylenediamine disappeared from the system. To this mixture was then added 25.4 parts of the p-formyl-N,N-dipropoxy-m-aminophenol produced in parts B above and the resultant composition was maintained at a temperature of about 90-95° C. for 1 hour. Hydrolysis with aqueous NAOH resulted in a bright yellow coumarin colorant represented by Formula (VII): ##STR8##

Workup

  1. additionwere then subsequently added
  2. temperatureThis mixture was heated to
  3. customproduced in parts B above and the resultant composition
  4. customHydrolysis with aqueous NAOH

Sources & evidence

ORD record
ord-18b31179da4d46ccb5378fcc016b8b15
Source dataset
uspto-grants-2000_03
Patent number
US06040482

Reaction notes

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