Carbamide Peroxide → 4-Hydroxystyrene 7,8-oxide

HRID 1684879Notes

Reaction equation

HRID 1684879 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.OO.NC(N)=[O:14].CC1(C)O[C@H]2[C@@H]3OC(C)(C)O[C@]3(C(O)=O)O[C@H]2CO1.O>ClCCl.O1CCCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[CH2:7][O:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31294Carbamide PeroxideHCID 624534-VinylphenolHCID 16211407alpha-L-xylo-2-Hexulofuranosonic acid, 2,3:4,6-bis-O-(1-methylethylidene)-, monohydrate

Product 1

HCID 1250894-Hydroxystyrene 7,8-oxideYield 66%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

Fifth recycle 4-Hydroxy styrene: 1 g, 8.3 mmol, urea hydrogen peroxide: 3 g, 32 mmol, Immobilized lipase: 87 mg, 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate: 0.3 g, 1.03 mmol, dry dichloromethane:tetrahydrofuran (4:1): 15 mL. Same procedure was followed as described in example ‘1’. Reaction time: 20 hours, Yield: 66%.

Workup

  1. customReaction time
  2. custom20 hours, Yield: 66%

Sources & evidence

ORD record
ord-b86ec42eca8e44ee86f800293e15d7e3
Source dataset
uspto-grants-2012_04
Patent number
US08148118B2

Reaction notes

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