Water → HCID 54539569, compound

HRID 1165097Notes

Reaction equation

HRID 1165097 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]1([OH:29])[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=1.B(F)(F)F.CCOCC.O>O1CCOCC1>[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][C:27]1[CH:26]=[CH:25][C:24]([OH:28])=[CH:23][C:22]=1[OH:29]

Participants

6

Reactant 4

HCID 962WaterHCID 5054ResorcinolHCID 8000Boron trifluoride etherateHCID 1453863,7,11,15-Tetramethylhexadec-2-en-1-ol

Product 1

HCID 54539569HCID 54539569, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,7,11,15-Tetramethyl-2-hexadecen-1-ol(14.8 g; 50 mmole) in 15 ml of dioxane was dropwise added to 11.0 g (100 mmole) of 1,3-benzenediol and 4.3 g (30 mmole) of boron trifluoride ethyl etherate in 30 ml of diozane at room temperature over one hour. After stirring the reaction solution at that temperature overnight, the solution was poured into 75 ml of water and was extracted with isopropyl ether (100 ml). The extract was washed with 200 ml of water (3 times) and 200 ml of saturated aqueous solution of sodium chloride (3 times) followed by drying it over anhydrous magnesium sulfate, distilling off the solvent and subjecting the resulting residue to silica gel column chromatography to thereby obtain 2.80 g of the title compound from the fractions eluted with hexane-ethyl acetate (3:1). Yield=14%.

Workup

  1. extractionwas extracted with isopropyl ether (100 ml)
  2. washThe extract was washed with 200 ml of water (3 times) and 200 ml of saturated aqueous solution of sodium chloride (3 times)
  3. dry with materialby drying it over anhydrous magnesium sulfate
  4. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-bb680a75db4847469e421074e04d1104
Source dataset
uspto-grants-1990_03
Patent number
US04906669

Reaction notes

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