Tetramethylammonium hydroxide → HCID 67593023, compound

HRID 1416990Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH3:9])=[CH:4][CH:3]=1.[OH-:24].C[N+](C)(C)C.Br[CH2:31][CH2:32][CH:33]1[O:38][CH2:37][CH2:36][CH2:35][O:34]1>C(#N)C.C(OCC)(=O)C>[O:34]1[CH2:35][CH2:36][CH2:37][O:38][CH:33]1[CH2:32][CH2:31][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:31][CH2:32][CH:33]3[O:38][CH2:37][CH2:36][CH2:35][O:34]3)=[CH:12][CH:11]=2)([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:31][CH2:32][CH:33]3[O:34][CH2:35][CH2:36][CH2:37][O:24]3)=[CH:21][CH:22]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

26.8 g of tris(4-hydroxyphenyl)ethane was dissolved in 180 ml of acetonitrile in a flask and added with 126 ml of tetramethylammonium hydroxide (25% aqueous solution) and then, with 39.4 ml of 2-(2-bromoethyl)-[1,3]-dioxane. The resulting solution was heated to 80° C. and stirred for 10 hours. The reactant mixture was diluted with 250 ml of ethyl acetate and washed with 300 ml of 5% aqueous sodium hydroxide solution and then, with 300 ml of saline. The organic layer was dried over magnesium sulfate, filtered and deprived of the solvent. The residue was crystallized in methanol, to give 46 g of 1,1,1-tris-[4-(2-[1,3]-dioxan-2-yl ethoxy)phenyl]ethane as a white powder (mp=101° C.), represented by the following formula. ##STR9##

Workup

washwashed with 300 ml of 5% aqueous sodium hydroxide solution
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
customThe residue was crystallized in methanol

Sources & evidence

ORD record: ord-8fee1f901dec4e208a173268dfd50e1b
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05916995

Reaction notes

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