Dimethylamine → HCID 22255910, compound

HRID 1611726Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[CH3:25])[CH:20]=O.[CH3:26][NH:27][CH3:28]>O>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:20]([N:27]([CH3:28])[CH3:26])[C:19]2[CH:22]=[CH:23][C:24]([CH3:25])=[C:17]([CH3:16])[CH:18]=2)[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 26.82 g (0.13 mol) of 2,4-di-tert-butylphenol, 17.44 g (0.13 mol) of 3,4-di-methylbenzaldehyde and 22.0 g (0.20 mol) of a 40% aqueous solution of dimethylamine is heated in a closed vessel at 140° C. for 10 hours, the internal pressure rising to 4 bar. After cooling to room temperature, the reaction mixture is poured into 100 ml of water and extracted twice 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 28.25 g (59%) of 2,4-di-tert-butyl-6-[dimethylamino-(3,4-dimethyl-phenyl)-methyl]-phenol, m.p. 82-85° C., (compound (201), Table 2). Molecular weight C25H37NO (367.58). Analysis, calculated: C 81.69; H 10.15; N 3.81%. Analysis, found: C 81.78; H 10.05; N 3.80%. 1HNMR (300 MHz, CDCl3, ppm): 1.18 (s, 9H); 1.43 (s, 9H); 2.21 (s, 6H); 2.24 (s, 6H); 4.27 (s, 1H); 6.74 (d, 1H); 7.11 (m, 4H); 12.43 (s, 1H

Workup

temperatureAfter cooling to room temperature
extractionextracted twice using ethyl acetate
dry with materialdried over sodium sulfate
concentrationconcentrated
customa vacuum rotary evaporator
customCrystallisation of the residue from isopropanol

Sources & evidence

ORD record: ord-8d86b26e1e55412fb9747df9e2f79a22
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989446B2

Reaction notes

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