2-Chlorotoluene → Benzoyl chloride

HRID 2254919Notes

Reaction equation

HRID 2254919 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:8])=[O:7])=[CH:4][CH:3]=1.[N+](C1C=CC(C(Cl)=O)=CC=1)([O-])=O.C1(C)C(Cl)=CC=CC=1.FC1C=C(C=CC=1)C(Cl)=O.BrC1C=CC(C(Cl)=O)=CC=1.FC(F)(F)C1C=CC(C(Cl)=O)=CC=1.C(Cl)C1C(OC)=CC=CC=1.C1(C)C=CC(Cl)=CC=1.ClC1C=CC=CC=1C(Cl)=O.IC1C=CC(C(Cl)=O)=CC=1.IC1C=CC=CC=1C(Cl)=O.C(C1C=CC(C(Cl)=O)=CC=1)C.FC1C=CC=CC=1C(Cl)=O.[N+](C1C=CC=CC=1C(Cl)=O)([O-])=O>>[C:6]([Cl:8])(=[O:7])[C:5]1[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=1

Participants

15

Reactant 14

HCID 72382-ChlorotolueneHCID 78104-ChlorotolueneHCID 85024-Nitrobenzoyl chlorideHCID 98082-Fluorobenzoyl chlorideHCID 118752-Nitrobenzoyl chlorideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 678794-Fluorobenzoyl chlorideHCID 685154-Bromobenzoyl chlorideHCID 691102-Chlorobenzoyl chlorideHCID 691122-Iodobenzoyl chlorideHCID 743734-Iodobenzoyl chlorideHCID 743763-Fluorobenzoyl chlorideHCID 814952-(Chloromethyl)anisoleHCID 853684-Ethylbenzoyl chloride

Product 1

HCID 7412Benzoyl chloride

Procedure

Substituting p-chlorobenzoyl chloride for benzoyl chloride in the above reaction yields p-chlorobenzoic acid, 2-tert-butylhydrazide; melting point 116°-122° C. Similarly, substituting p-fluorobenzoyl chloride, p-nitro- benzoyl chloride, o-toluyl chloride, m-fluorobenzoyl chloride, p-bromobenzoyl chloride, p-trifluoromethylbenzoyl chloride, o-anisyl chloride, p-toluyl chloride, o-chlorobenzoyl chloride, p-iodobenzoyl chloride, o-iodobenzoyl chloride, p-ethylbenzoyl chloride and o-fluorobenzoyl chloride, o-nitrobenzoyl chloride, for benzoyl chloride, yields respectively: p-fluorobenzoic acid, o-bromobenzoyl chloride, 2-tert-butylhydrazide; mp 136°-138° C.; p-nitrobenzoic acid, 2-tert-butylhydrazide; o-toluic acid, 2-tert-butylhydrazide; m-fluorobenzoic acid, 2-tert-butylhydrazide, mp 119°-120° C.; p-bromobenzoic acid, 2-tert-butylhydrazide; p-trifluoromethylbenzoic acid, 2-tert-butylhydrazide; anisic acid, 2-tert-butylhydrazide; p-toluic acid, 2-tert-butylhydrazide; o-chlorobenzoic acid, 2-tert-butylhydrazide; mp 68°-70° C.; o-iodobenzoic acid, 2-tert-butylhydrazide; p-ethylbenzoic acid, 2-tert-butylhydrazide; and o-fluorobenzoic acid, 2-tert-butylhydrazide; mp 58°-59° C.; o-nitrobenzoic acid, 2-tert-butylhydrazide; mp 116°-118° C.; o-bromobenzoic acid, 2-tert-butylhydrazide; mp 85°-87° C.; and N-methylanthranilic acid, 2-tert-butylhydrazide, mp 125°-129° C.

Sources & evidence

ORD record
ord-b92db675c581462d9a9a06d4887cf812
Source dataset
uspto-grants-1993_08
Patent number
US05237099

Reaction notes

Loading…