Water → HCID 13017653, compound

HRID 1065056Notes

Reaction equation

HRID 1065056 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:5])[CH3:4].[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([CH:19]2[O:21][CH2:20]2)=[CH:17][CH:16]=1.O>CS(C)=O>[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:20][CH:19]([OH:21])[C:18]2[CH:22]=[CH:23][C:15]([CH3:14])=[CH:16][CH:17]=2)=[CH:9][CH:8]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1983AcetaminophenHCID 24758Sodium hydrideHCID 1081112-(4-Methylphenyl)oxirane

Product 1

HCID 13017653HCID 13017653, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a mixture of 65% sodium hydride (4.4 g, 0.12 mole) and dimethylsulfoxide (60 ml) was added dropwise a solution of 4-acetamidophenol (XV: R=CH3) (15.1 g, 0.1 mole) in dimethylsulfoxide (30 ml). After cooling the resulting mixture to 8° to 10° C., a solution of 4-methylstyrene oxide (XIX) (13.4 g, 0.1 mole) in dimethylsulfoxide (30 ml) was added dropwise thereto over 1 hour, followed by reaction at 15° C. for 4 hours. Water was added to the reaction solution, and the precipitated crystals were filtered and recrystallized from ethanol to obtain 17.5 g of β-(4-acetamidophenoxy)-α-(4-methylphenyl)ethyl alcohol (XIV: R=CH3) as white crystals (yield, 61.4%).

Workup

  1. temperatureAfter cooling the resulting mixture to 8° to 10° C.
  2. customfollowed by reaction at 15° C. for 4 hours
  3. filtrationthe precipitated crystals were filtered
  4. customrecrystallized from ethanol
  5. customto obtain

Sources & evidence

ORD record
ord-ed81a99fb4b04f5aa9a0caedc7ee2a46
Source dataset
uspto-grants-1982_05
Patent number
US04328166

Reaction notes

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