Water → HCID 54396915, compound

HRID 1165094

Reaction equation

HRID 1165094 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:3][CH2:4]O.[C:22]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:27]=1[OH:36])([CH3:25])([CH3:24])[CH3:23].B(F)(F)F.CCOCC.O>O1CCOCC1>[C:32]([C:28]1[CH:29]=[C:30]([CH2:4][CH:3]=[C:2]([CH3:1])[CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH:31]=[C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:27]=1[OH:36])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 314052,6-Di-tert-butylphenolHCID 1453863,7,11,15-Tetramethylhexadec-2-en-1-ol

Product 1

HCID 54396915HCID 54396915, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3,7,11,15-tetramethyl-2-hexadecen-1-ol (2.97 g;10.0 mmole) in dioxane (8 ml) was dropwise added to a solution of 2,6-di-tert-butyl phenol (4.13 g;200 mmole) and boron trifluoride ethyl etherate (0.86 g;6.0 mmole) in dioxane (20 ml) at 40° C. over one hour. After stirring the resultant solution at that temperature for 2.5 hours, the reaction solution was poured into water (30 ml) and was then extracted once with ethyl acetate (20 ml). The extract was successively washed with 30 ml of 5% (w/v) aqueous sodium hydroxide solution containing 3% (w/v) sodium hydrosulfite (once), 30 ml of water (twice) and then 30 ml of saturated aqueous sodium chloride (once) and was dried over anhydrous magnesium sulfate. Then, the solvent and the unreacted 2,6-di-tert-butyl-phenol were distilled off and the resultant residue was subjected to silica gel column chromatography to obtain 440 mg (0.91 mmole) of 2,6,di-tert-butyl-4-(3,7,11,15,tetramethyl-2 -hexadecenyl)-phenol from the fractions eluted through the column with hexane-ethyl acetate (50:1). Yield=9.1%.

Workup

  1. extractionwas then extracted once with ethyl acetate (20 ml)
  2. washThe extract was successively washed with 30 ml of 5% (w/v) aqueous sodium hydroxide solution
  3. additioncontaining 3% (w/v) sodium hydrosulfite (once), 30 ml of water (twice) and then 30 ml of saturated aqueous sodium chloride (once) and
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationThen, the solvent and the unreacted 2,6-di-tert-butyl-phenol were distilled off

Sources & evidence

ORD record
ord-dc848e1dbc56433eb75f9df13c754907
Source dataset
uspto-grants-1990_03
Patent number
US04906669

Linked notes

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