O-Xylene → HCID 524499, compound

HRID 1911950Notes

Reaction equation

HRID 1911950 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=1C.ClC1CCCCC1=O>O>[CH2:1]([N:3]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 7670N-EthylanilineHCID 132032-Chlorocyclohexanone

Product 1

HCID 524499HCID 524499, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

266.2 g N-ethyl aniline was charged in a reactor along with 200 ml o-xylene. To this 132.5 g of 2-chloro-cyclohexanone was added over a period of 2 hours to obtain a clear solution which was then heated to 100° C. and stirred for 2 hours with water removal. The contents were further heated to 150-160° C. with simultaneous water removal by applying mild vacuum. The reaction mass was worked up as above to get 136 g crude 9-ethyl tetrahydrocarbazole with 96.8% GC purity.

Workup

  1. customto obtain a clear solution which

Sources & evidence

ORD record
ord-6a8c7b57e1fa4b74a9d2f5fe9536033d
Source dataset
uspto-grants-2013_12
Patent number
US08604219B2

Reaction notes

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