Benzenediazonium, 4-chloro-2-nitro-, chloride → 5-Chloro-2-nitro-2'-hydroxy-3',5'-di-(4-methoxy-alpha-cumyl)azobenzene

HRID 392561Notes

Reaction equation

HRID 392561 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([C:10]2[CH:15]=[C:14]([C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=2[OH:27])([CH3:9])[CH3:8])=[CH:5][CH:4]=1.[Cl-:30].Cl[C:32]1[CH:37]=[CH:36][C:35]([N+:38]#[N:39])=[C:34]([N+:40]([O-:42])=[O:41])[CH:33]=1>>[Cl:30][C:37]1[CH:32]=[CH:33][C:34]([N+:40]([O-:42])=[O:41])=[C:35]([N:38]=[N:39][C:12]2[CH:13]=[C:14]([C:16]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)([CH3:18])[CH3:17])[CH:15]=[C:10]([C:7]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:29][CH:28]=3)([CH3:8])[CH3:9])[C:11]=2[OH:27])[CH:36]=1

Participants

3

Reactant 2

HCID 10420991Benzenediazonium, 4-chloro-2-nitro-, chlorideHCID 226643902,4-Di-(4-methoxy-alpha-cumyl)phenol

Product 1

HCID 1356741115-Chloro-2-nitro-2'-hydroxy-3',5'-di-(4-methoxy-alpha-cumyl)azobenzene

Procedure

The title compound is prepared according to the procedure of Example 23 using 45 g of 2,4-di-(4-methoxy-α-cumyl)phenol prepared in Example 7 and 131 g of the diazonium salt solution of Example 11. The desired product is obtained in a yield of 49.1 g as a crimson red solid melting at 150-152° C. The structure is confirmed by 1Hnmr and mass spectroscopy analyses.

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-8ae4e77bcdc14f17af9614e5c7ec98f5
Source dataset
uspto-grants-2004_10
Patent number
US06800676B2

Reaction notes

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