Water → HCID 53662253, compound

HRID 1165099Notes

Reaction equation

HRID 1165099 reaction equation
C[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][OH:5].B(F)(F)F.CC[O:28][CH2:29][CH3:30].[OH2:31]>O1CCOCC1>[CH3:21][C:9]([CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:18])[CH2:19][CH2:7][CH2:8][CH:9]([CH3:21])[CH3:10])=[CH:8][CH2:7][C:6]1[C:2]([OH:31])=[CH:3][C:4]([OH:5])=[CH:30][C:29]=1[OH:28]

Participants

5

Reactant 3

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

Product 1

HCID 53662253HCID 53662253, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

3,7,11,15-Tetramethyl-2-hexadecen-1-ol (14.8 g;50 mmole) in dioxane (10 ml) was dropwise added to 16.2 g (100 mmole) of 1,3,5-benzenetriol·dihydrate and 4.3 g (30 mmole) of boron trifluoride ethyl etherate in dioxane (35 ml) at room temperature over one hour. After stirring the resulting reaction solution at that temperature overnight, it was further stirred at 50° C. for additional 3 hours, then poured into 150 ml of water and was extracted with 150 ml of isopropyl ether. The extract was washed twice with 150 ml of water and once with 150 ml of saturated aqueous solution of sodium chloride followed by drying it over anhydrous magnesium sulfate, distilling off the solvent and subjecting the resultant residue to silica gel column chromatography. Thus, 6.4 g of the title compound was recovered from the fractions eluted with hexane-ethyl acetate (2:1). Yield=32%.

Workup

  1. customthe resulting reaction solution at that temperature overnight, it
  2. stirringwas further stirred at 50° C. for additional 3 hours
  3. extractionwas extracted with 150 ml of isopropyl ether
  4. washThe extract was washed twice with 150 ml of water and once with 150 ml of saturated aqueous solution of sodium chloride
  5. dry with materialby drying it over anhydrous magnesium sulfate
  6. distillationdistilling off the solvent
  7. customThus, 6.4 g of the title compound was recovered from the fractions
  8. washeluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-01ac012a6c6d435cb02f9bf4b15108e0
Source dataset
uspto-grants-1990_03
Patent number
US04906669

Reaction notes

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