Hydrogen Peroxide → 4-(Phenethyl)benzoyl chloride

HRID 1699648Notes

Reaction equation

HRID 1699648 reaction equation
[O-][O-].[Na+].[Na+].[C:5]1([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1.S(Cl)(Cl)=O.C1(CCC2C=CC=CC=2)C(C(Cl)=[O:33])=CC=CC=1.[OH-].[Na+].OO.OO.[OH-].[Na+].[CH2:51]([C:59]1[CH:67]=[CH:66][C:62]([C:63]([Cl:65])=[O:64])=[CH:61][CH:60]=1)[CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>O1CCCC1.O>[CH2:14]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([O:13][O:64][C:63](=[O:33])[C:62]2[CH:66]=[CH:67][C:59]([CH2:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[CH:60][CH:61]=2)=[O:12])=[CH:9][CH:10]=1)[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1.[C:59]1([CH2:51][CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:60]=[CH:61][C:62]([C:63]([Cl:65])=[O:64])=[CH:66][CH:67]=1

Participants

12

Reactant 8

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 14803Sodium peroxideHCID 24386Thionyl ChlorideHCID 104894314-(2-Phenylethyl)benzoic acidHCID 149053692-(2-Phenylethyl)benzoyl chlorideHCID 186814834-(Phenethyl)benzoyl chlorideHCID 23682848Hydrogen peroxide sodium hydroxide

Product 2

HCID 186814834-(Phenethyl)benzoyl chlorideHCID 18681484Bis(4-(phenethyl)benzoyl) peroxide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

This peroxide was synthesized from the corresponding acid chloride and sodium peroxide. First, 4-bibenzylcarboxylic acid chloride was prepared from 4-bibenzylcarboxylic acid and thionyl chloride (see the synthesis of 2-bibenzylcarboxylic acid chloride above). The acid chloride was purified by vacuum distillation (bp=104-106° C./120-130, μHg), and solidified upon cooling. The synthesis of the peroxide was performed with NaOH/H2O2 and the acid chloride in tetrahydrofuran. Here, 12.0 ml 30% H2O2 was added to 4.8 g NaOH in 30.0 ml H2O and the solution cooled to 5° C. A solution of 2.0 g 4-(phenethyl)benzoyl chloride in 2.0 ml tetrahydrofuran was then added and the reaction mixture stirred for one hour. The crude peroxide was filtered off and recrystallized from chloroform/methanol, mp=145° C. (decomp.). The yield was 41%. The peroxide proved to be quite insoluble in common solvents, except for chloroform and large amounts of benzene. NMR δ(ppm): 2.9-3.0 (m, 8, —CH2—CH2—), 7.1-7.3, 7.9-8.0 (m, m, 18, aromatic H).

Workup

  1. distillationThe acid chloride was purified by vacuum distillation (bp=104-106° C./120-130, μHg)
  2. temperatureupon cooling
  3. customThe synthesis of the peroxide
  4. filtrationThe crude peroxide was filtered off
  5. customrecrystallized from chloroform/methanol, mp=145° C. (decomp.)

Sources & evidence

ORD record
ord-5b704de38e714c56a1e82625ccdb61b8
Source dataset
uspto-grants-2002_02
Patent number
US06348429B1

Reaction notes

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