Triethylamine → HCID 70476564, compound

HRID 2413022Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([OH:23])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][C:9]=2[C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:4])([CH3:3])[CH3:2].[P:24]([O:27][C:28]1[C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)[OH:30])(Cl)[OH:25].C(N(CC)CC)C>C1(C)C=CC=CC=1.CC(C)=O>[P:24]([OH:27])([OH:23])[OH:25].[C:1]([C:5]1[C:6]([C:31]2[CH:32]=[CH:33][CH:34]=[C:28]([OH:27])[C:29]=2[OH:30])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][C:9]=2[C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 6 °C

Procedure

6.0 weight parts of 3,6,8-tri-t-butylnaphthol was dissolved in 86.7 weight parts of dry toluene and the solution cooled to about 6° C. Under nitrogen, 3.36 weight parts of catechol phosphorochloridite was added to the solution. 1.95 weight parts of triethyl amine was added slowly to the cooled stirred solution. The reaction was allowed to continue for 16 hours at room temperature. 69 weight percent product was obtained. The reaction mixture was filtered, washed twice with water, dried over MgSO4 and rotoevaporated to remove all traces of toluene. An oil was obtained that solidified. This solid was stirred in acetone and a white powder was obtained that had a melting point of 140°-142° C. The expected structure was confirmed by infra red and nuclear magnetic resonance spectra. The molecular weight was confirmed by the field desorption/mass spectrum.

Workup

custom69 weight percent product was obtained
filtrationThe reaction mixture was filtered
washwashed twice with water
dry with materialdried over MgSO4
customto remove all traces of toluene
customAn oil was obtained that solidified
customa white powder was obtained

Sources & evidence

ORD record: ord-e1ae21f7e4f7487095932683f8d37ed4
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04495320

Reaction notes

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