4-Nitrophenol → Ethyl 2-(4-nitrophenoxy)tetradecanoate

HRID 1703449Notes

Reaction equation

HRID 1703449 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[CH2:11]([O:13][C:14](=[O:29])[CH:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:12]>CC(C)=O>[CH2:11]([O:13][C:14](=[O:29])[CH:15]([O:10][C:3]1[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:12]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 85791Tetradecanoic acid, 2-bromo-, ethyl ester

Product 1

HCID 54095639Ethyl 2-(4-nitrophenoxy)tetradecanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

153 g (1.1 mol) of p-nitrophenol, 1.3 liters acetone and 336 g (1.0 mol) of ethyl-α-bromo-tetradecanoate were placed in a 5-liter 3-necked flask and heated on a steam bath with stirring, for 60 hours. The product was filtered to remove inorganic salt and then the acetone was distilled off under vacuo. The residual oil was taken up in hexane, filtered, and concentrated under vacuo. Yield of Intermediate I was 361 g. TLC Analysis (benzene) showed only one spot, indicating a single product.

Workup

  1. temperatureheated on a steam bath
  2. filtrationThe product was filtered
  3. customto remove inorganic salt
  4. distillationthe acetone was distilled off under vacuo
  5. filtrationfiltered
  6. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-a514fbd097f841368793f2eca21dad84
Source dataset
uspto-grants-1978_11
Patent number
US04124396

Reaction notes

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