Toluene → HCID 54529216, compound

HRID 1611727Notes

Reaction equation

C1(C)C=CC=CC=1.FC(F)(F)C(O)=O.[C:15]([C:19]1[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[C:21]([CH:29](N(C)C)[C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([CH3:37])[CH:31]=2)[C:20]=1[OH:41])([CH3:18])([CH3:17])[CH3:16]>O>[C:15]([C:19]1[C:20](=[O:41])[C:21](=[CH:29][C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([CH3:37])[CH:31]=2)[CH:22]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)([CH3:16])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 110 °C

Procedure

60 ml of dry toluene and 2.9 g (25.5 mmol) of trifluoroacetic acid are added, under argon, to 6.24 g (17 mmol) of 2,4-di-tert-butyl-6-[dimethylamino-(3,4-dimethyl-phenyl)-methyl]-phenol(compound (201). Table 2), prepared according to Example 1a. The reaction mixture is then maintained at 110° C. for 6 hours. After colling to room temperature, the mixture is poured into 50 ml of water and extracted three times using ethyl acetate. The organic phases are combined, dried over sodium sulfate and concentrated using a vacuum rotary evaporator. Crystallisation of the residue from isopropanol yields 4.48 g (82%) of a mixture of 2,4-di-tert-butyl-6-(3,4-dimethyl-benzylidene)-cyclohexa-2,4-dienone (compound (301), Table 3) and the corresponding dimer (compound (401), Table 4), m.p. 214-217°C.

Workup

customprepared
customAfter colling to room temperature
extractionextracted three times
dry with materialdried over sodium sulfate
concentrationconcentrated
customa vacuum rotary evaporator
customCrystallisation of the residue from isopropanol

Sources & evidence

ORD record: ord-f3f62907598c4f36a34068a6e1c35e7c
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989446B2

Reaction notes

Loading…