Boron trifluoride etherate → HCID 54036300, compound

HRID 745475Notes

Reaction equation

HRID 745475 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH3:9])[CH:5]=[C:4]([OH:15])[CH:3]=1.O[C:17]([C:20]1[CH2:25][CH:24]=[C:23]([O:26][CH3:27])[CH2:22][CH:21]=1)([CH3:19])[CH3:18].B(F)(F)F.CCOCC>C1C=CC=CC=1>[CH3:27][O:26][C:23]12[CH2:22][CH:21]([C:20](=[C:17]([CH3:18])[CH3:19])[CH2:25][CH2:24]1)[C:3]1=[C:4]([OH:15])[CH:5]=[C:6]([CH:8]([CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH3:9])[CH:7]=[C:2]1[O:1]2

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 64542264-Methoxy-alpha,alpha-dimethylcyclohexa-1,4-diene-1-methanolHCID 54246356HCID 54246356, compound

Product 1

HCID 54036300HCID 54036300, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.05 g. of 1,3-dihydroxy-5-(5-methoxy-2-pentyl)- benzene and 1.06 g. (6 mmoles) of 1-(2-hydroxy-2-propyl)- 4methoxy-1,4-cyclohexadiene [R.A. Archer et. al. J. Org. Chem., 42, 2277 (1977)]are dissolved in 25 ml. of abs. benzene. 0.5 ml. (3.4 mmoles) of borontrifluoride etherate are added and the mixture is stirred at room temperature for 5 hours. Further 0.40 g. (2.4 mmoles) diene are added and the mixture is stirred overnight. The solution is poured off from the precipitated gum and extracted with 3 ×10 ml. of 1 N sodium hydroxide. The benzene solution is dried, evaporated and the residue is chromatographed on a column with a 8.1 mixture of benzene: ethyl acetate. The product is a colorless resin.

Workup

  1. dissolution, 42, 2277 (1977)]are dissolved in 25 ml
  2. stirringthe mixture is stirred overnight
  3. additionThe solution is poured off from the precipitated gum
  4. extractionextracted with 3 ×10 ml
  5. dry with materialThe benzene solution is dried
  6. customevaporated
  7. customthe residue is chromatographed on a column with a 8.1 mixture of benzene

Sources & evidence

ORD record
ord-e88e5a3343c7498daedc8d3eb4d59d66
Source dataset
uspto-grants-1986_07
Patent number
US04599327

Reaction notes

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