4-Hydroxybenzyl Alcohol → HCID 12963449, compound

HRID 1011447Notes

Reaction equation

HRID 1011447 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19]>CC(C)=O>[CH3:16][N:17]([CH3:21])[C:18](=[O:19])[O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 12963449HCID 12963449, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5 g (40.3 mmol) of 4-(hydroxymethyl)phenol in 500 mL of acetone was added finely powdered K2CO3 (27.83 g, 0.2 mol) and 3.71 mL (40.3 mmol) of N,N-dimethylcarbamoyl chloride. This mixture was heated under reflux overnight and then filtered. After evaporation of the solvent, a purification by column chromatography on silica gel with cyclohexane/iPrOH (9/1) and as eluent gave 7.16 g (yield: 91%) of compound of molecular formula C10H13NO3. Aspect: white powder.

Workup

  1. temperatureThis mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationfiltered
  4. customAfter evaporation of the solvent
  5. customa purification by column chromatography on silica gel with cyclohexane/iPrOH (9/1)

Sources & evidence

ORD record
ord-2e2ad779e7a940b591df4fab2abba649
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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