p-Nitroacetophenone → 1-(4-Nitrophenyl)ethan-1-ol

HRID 2106632Notes

Reaction equation

HRID 2106632 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][C:6](O)=[CH:5][CH:4]=1.Cl[C:11]([O:13]C(Cl)(Cl)Cl)=[O:12].[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]([OH:29])[CH3:28])=[CH:23][CH:22]=1)([O-:20])=[O:19].[CH3:30][C:31]([C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:32].[BH4-].[Na+]>C(O)C>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([CH:27]([O:29][C:11]([O:13][CH:1]=[CH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:12])[CH3:28])=[CH:25][CH:26]=1)([O-:20])=[O:19].[N+:39]([C:36]1[CH:35]=[CH:34][C:33]([CH:31]([OH:32])[CH3:30])=[CH:38][CH:37]=1)([O-:41])=[O:40]

Participants

8

Reactant 5

HCID 7487p-NitroacetophenoneHCID 10426DiphosgeneHCID 624534-VinylphenolHCID 5923761-(4-Nitrophenyl)ethan-1-olHCID 4311764Sodium borohydride

Product 2

HCID 5923761-(4-Nitrophenyl)ethan-1-olHCID 86743985HCID 86743985, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Poly(4-(1-(4-nitrophenyl)ethyloxycarbonyloxystyrene (FIG. 7A) was prepared from poly(4-hydroxystyrene), available from the Maruzen Oil Company, by treatment with trichloromethyl chloroformate and 1-(4-nitrophenyl)ethanol. Specifically, a solution of 4-nitroacetophenone in ethanol was treated with sodium borohydride at about 0° C. for about 4 hours, then quenched by the addition of water. Extraction with ethyl acetate followed by drying and concentration provided crude 1-(4-nitrophenyl)ethanol, which was purified by recrystallization. A solution of 1-(4-nitrophenyl)ethanol in tetrahydrofuran (THF) was added to a solution of excess trichloromethyl chloroformate and triethylamine in THF, stirred at reflux for about 2 hours, filtered to remove the solids, and concentrated under vacuum. The resulting oil was dissolved in THF and added to a solution of poly(4-hydroxystyrene), 4-dimethylaminopyridine, and triethylamine in THF. This mixture was stirred for about 18 hours at about 20° C., filtered, then concentrated. The residue was dissolved in methylene chloride, treated with aqueous sodium bicarbonate solution, and the polymer was precipitated by addition into methanol.

Workup

  1. customquenched by the addition of water
  2. extractionExtraction with ethyl acetate
  3. customby drying
  4. concentrationconcentration

Sources & evidence

ORD record
ord-9f1650a809234420b328552c7bd382c2
Source dataset
uspto-grants-1990_06
Patent number
US04931379

Reaction notes

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