Naringin → Naringenin

HRID 848716

Reaction equation

HRID 848716 reaction equation
C[C@@H]1O[C@@H](O[C@H]2[C@H]([O:15][C:16]3[CH:17]=[C:18]([OH:34])[C:19]4[C:25](=[O:26])[CH2:24][C@@H:23]([C:27]5[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=5)[O:22][C:20]=4[CH:21]=3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O>Cl>[CH:32]1[C:27]([C@H:23]2[O:22][C:20]3[CH:21]=[C:16]([OH:15])[CH:17]=[C:18]([OH:34])[C:19]=3[C:25](=[O:26])[CH2:24]2)=[CH:28][CH:29]=[C:30]([OH:33])[CH:31]=1

Participants

3

Reactant 1

HCID 442428Naringin2×

Product 1

HCID 439246Naringenin

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

616.5 grams naringin were added to a round bottomed flask, followed by the addition of about one liter of 0.5 N hydrochloric acid. Upon stirring and refluxing, the naringin dissolves to form a yellow to red-brown solution. While a brown gummy or oily material initially forms, it eventually disappears. As the reaction proceeds, a yellow solid precipitates. The reaction time is approximately 2 to 4 hours. The solution is cooled, and the yellow solid filtered and washed with copious amounts of water until the washings are no longer acidic. The amount of naringenin produced is about 160 grams.

Workup

  1. temperaturerefluxing
  2. customto form a yellow to red-brown solution
  3. customAs the reaction proceeds
  4. customa yellow solid precipitates
  5. temperatureThe solution is cooled
  6. filtrationthe yellow solid filtered
  7. washwashed with copious amounts of water until the washings

Sources & evidence

ORD record
ord-29a10da464654caca79df4dcc547a114
Source dataset
uspto-grants-1981_10
Patent number
US04297348

Linked notes

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