4-Nitrophenol → 4-Nitrophenyl tetradecyl ether

HRID 1728859Notes

Reaction equation

HRID 1728859 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[OH-].[Na+].C1(C)C=CC=CC=1>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.O>[CH2:25]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 1140TolueneHCID 8208Myristyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 103370514-Nitrophenyl tetradecyl ether

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 75 g of 4-nitrophenol, 149.5 g of 1-bromotetradecane, 26.96 g of sodium hydroxide, 2.18 g of trioctyl methylammonium chloride, 400 ml of toluene and 400 of water is heated at reflux for 65 hours. The organic layer is separated, washed with 1N sodium hydroxide and dilute hydrochloric acid, dried and concentrated in vacuo. The residue is recrystallized from petroleum ether to give the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 65 hours
  3. customThe organic layer is separated
  4. washwashed with 1N sodium hydroxide and dilute hydrochloric acid
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue is recrystallized from petroleum ether

Sources & evidence

ORD record
ord-325349b4896b4f69b5ebbfe7af2247d1
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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