Phenol → HCID 20300979, compound

HRID 1733206Notes

Reaction equation

HRID 1733206 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Na].C1(O)C=CC=CC=1.[O:18]1[CH2:33][CH:19]1[CH2:20][N:21]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:22][CH:23]1[O:25][CH2:24]1>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:24][CH:23]2[CH2:22][N:21]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:20][CH:19]([CH2:33][OH:18])[O:25]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 90154-MethoxyphenolHCID 5360545Sodium2×HCID 14385393HCID 14385393, compound

Product 1

HCID 20300979HCID 20300979, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6.21 G of p-methoxyphenol (0.05 mole Aldrich) is dissolved in 150 ml of dry dioxane and 0.4 g of finely cut sodium is added to the mixture. Stirring is continued for 1 hour after which all of the sodium is reacted with the phenol. Then 10.96 g (0.05 mole) N,N-bis(2,3-epoxypropyl)benzylamine is added and the mixture stirred for 1/2 hour under nitrogen. A flask is fitted with a reflux condenser and the mixture added and heated at reflux for 18 hours. After cooling to room temperature, the entire mixture is poured into 300 ml of water and stirred for 1/2 hour. 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 and 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 of the title A compound (69%). The 11.8 g of product is dried in vacuo to give the title A as a clear colorless oil.

Workup

  1. stirringthe mixture stirred for 1/2 hour under nitrogen
  2. customA flask is fitted with a reflux condenser
  3. additionthe mixture added
  4. temperatureheated
  5. temperatureat reflux for 18 hours
  6. stirringstirred for 1/2 hour
  7. extractionThe aqueous mixture is extracted with 3×125 ml portions of chloroform
  8. washwashed with 200 ml of water and 200 ml of saturated NaCl solution
  9. dry with materialThe CHCl3 layer is then dried over anhydrous NaSO4
  10. customevaporated in vacuo
  11. customto yield 15.4 g (90%) of crude product as a pale yellow oil
  12. customThe oil is chromatographed on 300 g of neutral Alumina III

Sources & evidence

ORD record
ord-051231701a244ed5a0a8250789280194
Source dataset
uspto-grants-1980_12
Patent number
US04241059

Reaction notes

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