2,4-Imidazolidinedione, 5,5-bis(2-(phenylmethoxy)phenyl)- → 2,4-Imidazolidinedione, 5,5-bis(2-hydroxyphenyl)-

HRID 1278257Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28]CC2C=CC=CC=2)[NH:19][C:18](=[O:20])[NH:17][C:16]1=[O:21])C1C=CC=CC=1>[C].[Pd].O1CCOCC1>[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[NH:19][C:18](=[O:20])[NH:17][C:16]1=[O:21]

Participants

Conditions

Temperature: 80 °C

Procedure

11.0 Grams of 5,5-bis(2-benzyloxyphenyl)hydantoin (Example 12) were reduced in 150 ml. of dioxane in the presence of 2 g of palladium-carbon catalyst in an autoclave under a hydrogen pressure of 10 Kg/cm2 at room temperature. After completion of the hydrogen absorption, the whole was heated at 80° C. under a hydrogen pressure of 10 Kg/cm2 for about 5 hours. The reaction liquid was subjected to filtration to remove the catalyst and concentrated under reduced pressure and the resulting precipitates were filtered out. The product was recrystallized from a mixture of acetone-chloroform to obtain 3.4 g of 5,5-bis(2-hydroxyphenyl)hydantoin in the form of white crystals.

Workup

customat room temperature
customAfter completion of the hydrogen absorption
customThe reaction liquid
filtrationwas subjected to filtration
customto remove the catalyst
concentrationconcentrated under reduced pressure
customthe resulting precipitates
filtrationwere filtered out
customThe product was recrystallized from a mixture of acetone-chloroform

Sources & evidence

ORD record: ord-8934dc9f3cb74bf8bd79a9af0a003ed8
Source dataset: uspto-grants-1981_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04281009

Reaction notes

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