Chlorobenzene → HCID 22417752, compound

HRID 1720318Notes

Reaction equation

[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.[Sn](Cl)(Cl)(Cl)Cl.CN1CCNCC1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=1[CH3:1].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=2[CH3:1])=[CH:28][CH:27]=1

Participants

Reactant 4

HCID 7964Chlorobenzene

HCID 24287Tin tetrachloride

HCID 531671-Methylpiperazine

HCID 902892-Methyl-3-nitrobenzyl alcohol

Product 2

HCID 22417698HCID 22417698, compoundYield 24%

HCID 22417752HCID 22417752, compoundYield 41%

Procedure

A mixture of 25 g (0.15 mol) of 2-methyl-3-nitrobenzyl alcohol and 25 ml (0.22 mol) of tintetrachloride in 250 ml of chlorobenzene is refluxed for 3 hours with stirring. After cooling 50 ml of N-methylpiperazine is slowly instilled. The precipitate is suctioned off and washed several times with ethyl acetate. The combined filtrates are dried on sodium sulfate and concentrated by evaporation and the temperature must not rise above 160° C. The residue (39 g) with a mixture of 33 parts of cyclohexane and 1 part of ethyl acetate is subjected twice to a pressure column chromatography. Thus 9.3 g (24%) of 2-(2-chlorobenzyl)-6-nitrotoluene, melting point 54°-56° C., and 16 g (41%) of 2-(4-chlorobenzyl)-6-nitrotoluene, melting point 62°-63° C. are obtained.

Workup

temperatureis refluxed for 3 hours
washwashed several times with ethyl acetate
customThe combined filtrates are dried on sodium sulfate
concentrationconcentrated by evaporation
customrise above 160° C
additionThe residue (39 g) with a mixture of 33 parts of cyclohexane and 1 part of ethyl acetate

Sources & evidence

ORD record: ord-feb2159c07544fabb4d01d70f87501b9
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506234

Reaction notes

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