Hydrochloric Acid → 5,5-Bis(4-hydroxyphenyl)hydantoin

HRID 1278256Notes

Reaction equation

HRID 1278256 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[C-]#[N:18].[K+].[C:20](=[O:23])([O-])[O-].[NH4+].[NH4+].[CH:26]([NH2:28])=[O:27].Cl>O>[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]2([C:8]3[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=3)[NH:18][C:26](=[O:27])[NH:28][C:20]2=[O:23])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 713FormamideHCID 9032Potassium CyanideHCID 691504,4'-DihydroxybenzophenoneHCID 517111Ammonium Carbonate

Product 1

HCID 1488755,5-Bis(4-hydroxyphenyl)hydantoin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

100 Grams of 4,4'-dihydroxybenzophenone, 152.1 g of potassium cyanide and 426.3 g of ammonium carbonate were heated to 120° C. together with 750 ml. of formamide and 150 ml. of water with stirring in an autoclave for 48 hours. The reaction liquid was made acidic with concentrated hydrochloric acid, mixed with water and allowed to stand overnight. The precipitates thus formed were filtered out. The precipitates were decolorized by active carbon and recrystallized from 50% methanol to obtain 111.4 g of 5,5-bis(4-hydroxyphenyl)hydantoin in the form of white crystals.

Workup

  1. customThe reaction liquid
  2. customThe precipitates thus
  3. customformed
  4. filtrationwere filtered out
  5. customrecrystallized from 50% methanol

Sources & evidence

ORD record
ord-e76319feab26461eaadea0e8e0d9208d
Source dataset
uspto-grants-1981_07
Patent number
US04281009

Reaction notes

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