Water → HCID 13374527, compound

HRID 364971Notes

Reaction equation

HRID 364971 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:16][CH2:17][N:18]([CH3:24])[C:19](=[O:23])[O:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:16][CH2:17][N:18]([CH3:24])[C:19](=[O:23])[O:20][CH2:21][CH3:22])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 12882312HCID 12882312, compound

Product 1

HCID 13374527HCID 13374527, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

18.6 g of p-phenoxyphenol are dissolved in 100 ml of dimethylformamide. 18.2 g of ethyl (2-chloroethyl)-methylcarbamate and 27.6 g of potassium carbonate are added thereto and the reaction mixture is heated at 80° C. while stirring for 15 hours. The reaction mixture is poured into 300 ml of water and extracted with diethyl ether. The ether extract is washed with semi-saturated and saturated sodium chloride solution, dried over sodium sulfate and evaporated. Chromatography on silica gel using n-hexane/ethyl acetate (9:1) as the eluent yields ethyl [2-(p-phenoxyphenoxy)ethyl]methylcarbamate; nD20 =1.5503.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. washis washed with semi-saturated and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2ad43a6a3062439c9148410ae35ad0e7
Source dataset
uspto-grants-1986_08
Patent number
US04607051

Reaction notes

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