Benzene → Butyrophenone

HRID 256211

Reaction equation

HRID 256211 reaction equation
C(C1C=CC=CC=1C=C)=C.[CH:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17](Cl)(=[O:21])[CH2:18][CH2:19][CH3:20]>[Cl-].[Al+3].[Cl-].[Cl-]>[CH2:18]([C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:21])[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 241BenzeneHCID 8855Butyryl chlorideHCID 666661,2-Diethenylbenzene

Product 1

HCID 10315Butyrophenone

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

About 50 grams of resin beads of polystyrene that has been copolymerized with about 1% divinylbenzene are stirred at room temperature for about 2 hours in butyryl chloride with aluminum chloride as a catalyst, namely Friedel-Crafts conditions. Reaction occurs with the benzene moieties on the resin to form butyrophenone or propylphenylketone. These resulting ketone moieties are then subjected to the Leukardt-Wallach reduction amination reaction using N-propyl formamide to produce N-propyl α-aminobenzyl moieties. The step-by-step synthesis of the nonapeptide as set forth in Example I is repeated. Cleavage, deprotection and purification are carried out under the same conditions and are found to produce the nonapeptide amide having the following formula:

Workup

  1. customReaction

Sources & evidence

ORD record
ord-391515ef7ed54614934d87ce74b4052c
Source dataset
uspto-grants-1987_10
Patent number
US04701499

Linked notes

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