Hydrochloric Acid → 2-(2',4'-Dichlorophenyl)-5,5-dimethyl-1,3-cyclohexanedione

HRID 46783Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](N)[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14](=[O:15])[CH2:13][C:12]([CH3:17])([CH3:16])[CH2:11][C:10]1=[O:18].[ClH:19].N([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:19])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14](=[O:15])[CH2:13][C:12]([CH3:17])([CH3:16])[CH2:11][C:10]1=[O:18]

Participants

Conditions

Temperature: 10 °C

Procedure

A suspension of 5.00 g (0.0188 mol) of 2-(2'-chloro-4'-aminophenyl)-5,5-dimethyl-1, 3-cyclohexanedione in 75 ml of water containing 4.0 ml of concentrated HCl was stirred and heated almost to boiling for 10 min., then cooled to 10° C. and an additional 7 ml of conc. HCl added and the solution cooled to 0°-5° C. A solution of 2.00 g (0.0282 mol) of sodium nitrite in 6.0 ml of water was added dropwise to the amine hydrochloride solution while maintaining the temperature at 0°-5° C. When all the NaNO2 solution had been added, the diazonium salt solution was stirred for 30 min. at 0° C.

Workup

temperatureheated almost
temperaturethe solution cooled to 0°-5° C
temperaturewhile maintaining the temperature at 0°-5° C

Sources & evidence

ORD record: ord-018d4c7fab2549ea82c93b88660bde5a
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04175135

Reaction notes

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