Hydrochloric Acid → 1-Chloro-2,6-diethyl-4-methylbenzene

HRID 1662307Notes

Reaction equation

HRID 1662307 reaction equation
[ClH:1].[CH2:2]([C:4]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:5]=1N)[CH3:3].N(OCCC(C)C)=O>ClC1C=CC=CC=1Cl>[Cl:1][C:5]1[C:4]([CH2:2][CH3:3])=[CH:10][C:9]([CH3:11])=[CH:8][C:7]=1[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8053Isoamyl NitriteHCID 905362,6-Diethyl-p-toluidine

Product 1

HCID 594889821-Chloro-2,6-diethyl-4-methylbenzeneYield 90%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
45 °C

Procedure

Gaseous hydrogen chloride (1.05 equiv.) is fed into a solution of 2,6-diethyl-4-methylaniline (1.00 equiv.) in o-dichlorobenzene, allowing the pot temperature to rise to 70° C. The resulting salt suspension is cooled to 45° C. Isoamyl nitrite (1.05 equiv.) and additional gaseous hydrogen chloride (0.50 equiv.) are fed subsurface simultaneously at 45-50° C. over a 2-hour period to afford 1-chloro-2,6-diethyl-4-methylbenzene in 90-93% yield. 20% sodium hydroxide (0.50 equiv.) is added to adjust the pH to 10-12. The bottom aqueous phase is separated off. Isoamyl alcohol and o-dichlorobenzene are stripped off to produce the crude 1-chloro-2,6-diethyl-4-methylbenzene material. The product can be further purified by vacuum distillation at 85° C./5 mmHg to give an assay of 97-99%.

Workup

  1. customto rise to 70° C
  2. customsimultaneously at 45-50° C.
  3. customover a 2-hour

Sources & evidence

ORD record
ord-d2f802b7575e42a5a16403d569572ed7
Source dataset
uspto-grants-2011_10
Patent number
US08030529B2

Reaction notes

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