Quinone → HCID 12657569, compound

HRID 1879355Notes

Reaction equation

HRID 1879355 reaction equation
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[CH:9]1[CH2:15][CH2:14][CH2:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH:11]12[CH:10]=[CH:9][CH:15]([CH2:14][CH2:13][CH2:12]1)[CH:5]1[CH:6]2[C:1](=[O:8])[CH:2]=[CH:3][C:4]1=[O:7]

Participants

4

Reactant 2

HCID 4650QuinoneHCID 199691,3-Cycloheptadiene

Product 1

HCID 12657569HCID 12657569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17.2 g of 1,4-benzoquinone in 240 mL DCM were added 7.6 mL of BF3-diethyletherate followed by 17.2 mL of 1,3-cycloheptadiene at −20° C. The cooling bath was removed after 20 min and the mixture furthermore stirred for 30 min at rt. The reaction mixture was then poured into ice cold KOH (30% aq.) solution and it was vigorously stirred for 10 min. After filtration over celite the organic phase was dried over K2CO3 and concentrated in vacuo to obtain 21.7 g of the desired compound as mixture of stereoisomers as brown solid.

Workup

  1. customThe cooling bath was removed after 20 min
  2. additionThe reaction mixture was then poured into ice cold KOH (30% aq.) solution and it
  3. stirringwas vigorously stirred for 10 min
  4. filtrationAfter filtration over celite the organic phase
  5. dry with materialwas dried over K2CO3
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a908e6b462d4d7aa16ec6c1d149f4ff
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Reaction notes

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