Boron trifluoride etherate → HCID 18609528, compound

HRID 1789605Notes

Reaction equation

HRID 1789605 reaction equation
C([O:4][CH2:5]/[C:6](/[CH3:26])=[CH:7]/[CH2:8][C:9]1[C:14]([CH3:15])=[C:13]([O:16][C:17](=[O:19])[CH3:18])[C:12]([CH3:20])=[C:11]([CH3:21])[C:10]=1[O:22][C:23](=[O:25])[CH3:24])(=O)C.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>CO>[C:23]([O:22][C:10]1[C:11]([CH3:21])=[C:12]([CH3:20])[C:13]([O:16][C:17](=[O:19])[CH3:18])=[C:14]([CH3:15])[C:9]=1[CH2:8]/[CH:7]=[C:6](\[CH3:26])/[CH2:5][OH:4])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 18609525HCID 18609525, compound

Product 1

HCID 18609528HCID 18609528, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.0 g of (E)-4-(2',5'-diacetoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenyl acetate are dissolved in 50 ml of methanol and treated with 0.2 g of boron trifluoride etherate. The mixture is boiled at reflux for 4 hours, then cooled to room temperature and poured into aqueous sodium bicarbonate solution. The aqueous solution is extracted with diethyl ether, and the ether phase is washed in sequence with sodium bicarbonate solution and sodium chloride solution, dried over anhydrous sodium sulphate and evaporated to dryness. From the residue (4.6 g) there are obtained by column chromatography (silica gel, diethyl ether/n-hexane/methanol) 4.0 g of (E)-4-(2',5'-diacetoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol in the form of white crystals, m.p. 118°-120° C.

Workup

  1. temperatureat reflux for 4 hours
  2. extractionThe aqueous solution is extracted with diethyl ether
  3. washthe ether phase is washed in sequence with sodium bicarbonate solution and sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-fd416b8ee8f64b7291e0922cc5033067
Source dataset
uspto-grants-1987_08
Patent number
US04689427

Reaction notes

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