1,3-Butadiene → HCID 15657643, compound

HRID 1460574Notes

Reaction equation

HRID 1460574 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH2:2]1.[CH2:16]=[CH:17][CH:18]=[CH2:19]>C1(C)C=CC=CC=1>[CH:10]1[C:5]2[C:4]3([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:16][CH:17]=[CH:18][CH2:19][CH:3]3[CH2:2][O:1][C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 15657629HCID 15657629, compound

Product 1

HCID 15657643HCID 15657643, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of the product of Example 15 (20.3 g) was dissolved in toluene (100 ml) and to it was added BHT (0.5 g) and butadiene (73 g) the reaction vessal was pressurized with nitrogen (1900 psi) and heated to 150° C. for 6 days. The resulting syrup (40 g) was partitioned between heptane and acetonitrile. The acetonitrile solution was washed with fresh heptane then evaporated in vacuo. The heptane phase was extracted with fresh acetonitrile which was evaporated to give a further recovery of crude product. The resulting oils were chromatographed on silical gel (eluting with ethyl acetate:heptane (1:60)), to give the title compound as a crystalline solid (10.1 g, 38%), mp 88° C.

Workup

  1. customThe resulting syrup (40 g) was partitioned between heptane and acetonitrile
  2. washThe acetonitrile solution was washed with fresh heptane
  3. customthen evaporated in vacuo
  4. extractionThe heptane phase was extracted with fresh acetonitrile which
  5. customwas evaporated
  6. customto give a further recovery of crude product
  7. customThe resulting oils were chromatographed on silical gel (eluting with ethyl acetate:heptane (1:60))

Sources & evidence

ORD record
ord-524d4af9af994bc58a7191bcc2beb972
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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