Water → HCID 20300979, compound

HRID 1733205Notes

Reaction equation

HRID 1733205 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Na].[O:11]1[CH2:26][CH:12]1[CH2:13][N:14]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:15][CH:16]1[O:18][CH2:17]1.O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:17][CH:16]2[CH2:15][N:14]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:13][CH:12]([CH2:26][OH:11])[O:18]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 90154-MethoxyphenolHCID 5360545SodiumHCID 14385393HCID 14385393, compound

Product 1

HCID 20300979HCID 20300979, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6.21 g of p-methoxyphenol (0.05 mole) in 150 ml of dry dioxane is stirred under dry nitrogen and 0.4 g of finely cut sodium added. The mixture is stirred at room temperature for 1 hour and then 10.96 g of N,N-bis(2,3-epoxypropyl)benzylamine (0.05 mole) is added to the reaction mixture. The mixture is then heated at reflux for 18 hours, cooled to room temperature and poured into 300 ml of water. The aqueous mixture is extracted with 3×125 ml portions of chloroform. The CHCl3 extracts are combined, washed with 200 ml of water and 200 ml of saturated NaCl solution. The CHCl3 layer is then dried over anhydrous NaSO4, evaporated in vacuo to yield 15.4 g (90%) of crude product as a pale yellow oil. The oil is chromatographed on 300 g of neutral Alumina III to give 11.8 g (69%) of wet product (eluted with 650 ml of chloroform and 200 ml of 2% methanolic chloroform). 11.8 g of wet product is dried in vacuo to give the desired product as a clear colorless oil.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 18 hours
  3. temperaturecooled to room temperature
  4. extractionThe aqueous mixture is extracted with 3×125 ml portions of chloroform
  5. washwashed with 200 ml of water and 200 ml of saturated NaCl solution
  6. dry with materialThe CHCl3 layer is then dried over anhydrous NaSO4
  7. customevaporated in vacuo
  8. customto yield 15.4 g (90%) of crude product as a pale yellow oil
  9. customThe oil is chromatographed on 300 g of neutral Alumina III

Sources & evidence

ORD record
ord-75f3a41628bf410c8d2ed97eec097c20
Source dataset
uspto-grants-1980_12
Patent number
US04241059

Reaction notes

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