Acetic Acid → HCID 21288658, compound

HRID 622318Notes

Reaction equation

HRID 622318 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].[H-].[Na+].[C:26]([OH:29])(=O)[CH3:27]>C1COCC1>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([O:13][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([O:29][C:26]2[CH:27]=[CH:3][C:2]([CH2:15][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])=[CH:1][CH:7]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69451-Chloro-2-nitrobenzene2×HCID 171324-n-Hexylphenol2×HCID 24758Sodium hydride

Product 2

HCID 21288658HCID 21288658, compoundYield 34%HCID 21292482HCID 21292482, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

The plasticizer 2-nitrophenyl 4-hexylphenyl ether (NPHPE) is synthesized by reacting p-hexylphenol (available from Kodak Lab. Chem., catalog No. 14,319) with 2-chloronitrobenzene (available from Aldrich Chem. Co., catalog No. C5,910-6). 1.44 g (0.06 mol) of sodium hydride is suspended in 75 ml of THF under N2. 9.01 g (0.05 mol) of p-hexylphenol are dissolved in 25 ml of THF and added dropwise to the suspension. 7.86 (0.05 mol) of 2-chloronitrobenzene are dissolved in 25 ml of THF and added dropwise to the reaction mixture; the resultant mixture is refluxed for 88 hours. Following reflux 3 ml of acetic acid are added, and the reaction is filtered through filter cel, concentrated, chromatographed twice on silical gel, and Kugelrohr distilled at 0.01 mm Hg, 140°-150° C., to yield 4.7 g (34% yield) of 2-nitrophenl 4-hexylphenyl ether as an orange oil.

Workup

  1. additionadded dropwise to the suspension
  2. additionadded dropwise to the reaction mixture
  3. additionare added
  4. filtrationthe reaction is filtered
  5. filtrationthrough filter cel
  6. concentrationconcentrated
  7. customchromatographed twice on silical gel, and Kugelrohr
  8. distillationdistilled at 0.01 mm Hg, 140°-150° C.

Sources & evidence

ORD record
ord-0792d5cbf3a54cdca144b3b724fa96fa
Source dataset
uspto-grants-1988_09
Patent number
US04770759

Reaction notes

Loading…