Nitrogen → HCID 13741940, compound

HRID 745296Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])[CH2:8][CH2:9][C:10](OC)=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O-:23].[Na+].N#N.[OH:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][OH:49])=[CH:42][CH:41]=2)([CH3:39])[CH3:38])=[CH:33][CH:32]=1>O>[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])[CH2:8][CH2:9][C:10]([O:49][CH2:48][CH2:47][O:46][C:43]1[CH:42]=[CH:41][C:40]([C:37]([C:34]2[CH:33]=[CH:32][C:31]([O:30][CH2:29][CH2:28][O:27][C:10](=[O:11])[CH2:9][CH2:8][C:7]3[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:22]([OH:23])=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=3)=[CH:36][CH:35]=2)([CH3:39])[CH3:38])=[CH:45][CH:44]=1)=[O:11])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

Methyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate (6.42 g) was added to a flask equipped with a reflux condenser heated to 65° C. with hot water. The material was heated to 140° C. under N2 with magnetic stirring. Sodium methoxide (0.054 g) was added and a vacuum (10 mm) was applied. After 15 min., the vacuum was broken with N2 and 2,2-bis[4-(2-hydroxy)ethoxyphenyl]propane (3.16 g) was added. Vacuum was reapplied and temperature was slowly increaded to 160° C. After 4 hrs., the reaction was quenched with acetic acid and crystallized from isopropanol to give 7.5 g (89%) of the desired product, mp 104°-106° C.

Workup

customequipped with a reflux condenser
additionwas added
customwas slowly increaded to 160° C
waitAfter 4 hrs
custom, the reaction was quenched with acetic acid
customcrystallized from isopropanol

Sources & evidence

ORD record: ord-e2b46289d0774689bb23928000f207c2
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04598113

Reaction notes

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