Hydroquinone → HCID 11228865, compound

HRID 570024Notes

Reaction equation

HRID 570024 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.[C:7](=[O:11])([O:9][CH3:10])[NH2:8].C1(C=CC(O)=CC=1)O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:10][O:9][C:7]([NH:8][C:2](=[CH2:4])[C:1]([OH:6])=[O:5])=[O:11]

Participants

7

Reactant 5

HCID 785HydroquinoneHCID 962WaterHCID 1060Pyruvic AcidHCID 6101p-Toluenesulfonic acidHCID 11722Methyl Carbamate

Product 1

HCID 11228865HCID 11228865, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution pyruvic acid (4.40 g, 50.0 mmol), methyl carbamate (3.75 g, 50.0 mmol), hydroquinone (used for a polymerization inhibitor, 0.05 g), and p-toluene sulfonic acid (50 mg) in 30 ml benzene is refluxed in a 100 ml round bottom flask to which is attached a Dean-Stark trap. The system is exposed to air during the reaction. After 2 hours, 25 minutes, 0.60 ml water (33 mmol) accumulates in the trap. The yellow solution is hazy while warm, but a small amount of gelatinous precipitate accumulated upon cooling. The suspension is filtered and is evaporated. Proton nuclear magnetic resonance spectrosopy confirms the presence of the title compound; (CDCl3, ppm) 10.0-10.5 (1H, broad singlet), 5.4 (1H, broad singlet), 5.1 (1H, broad singlet), 4.5-5.0 (1H, broad singlet), 3.9 (3H, singlet).

Workup

  1. temperatureis refluxed in a 100 ml round bottom flask to which
  2. customThe system is exposed to air during the reaction
  3. temperaturewhile warm
  4. temperatureupon cooling
  5. filtrationThe suspension is filtered
  6. customis evaporated

Sources & evidence

ORD record
ord-85493bc3bf2742478e2e75cf9d5515b6
Source dataset
uspto-grants-1988_03
Patent number
US04734453

Reaction notes

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