Acetone → 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)

HRID 400277Notes

Reaction equation

HRID 400277 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([OH:9])=[CH:4][C:3]=1[OH:10].[CH3:11][C:12]([CH3:14])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O1C[CH2:32][CH2:31][CH2:30]1>>[CH3:11][C:12]1([CH3:14])[O:10][C:3]2[CH:4]=[C:5]3[O:9][C:31]([CH3:32])([CH3:30])[O:8][C:6]3=[CH:7][C:2]=2[O:1]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 14812Phosphorus oxide (P4O10)HCID 694641,2,4,5-Benzenetetrol

Product 1

HCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)Yield 48%

Procedure

18.6 g of the 1,2,4,5-tetrahydroxybenzene prepared according to Example 4 (0.13 mole) and 70 ml acetone (58.6 g, 1.0 mole) was dissolved in 1 1 tetrahydrofuran. 168 g P2O5 (1.18 mole) was added to the vigorously stirred mixture in portions as fast as possible. The mixture was heated to reflux for 4 hours. After cooling to room temperature the solids were filtered with suction and washed with 0.5 L ether. The combined filtrates were treated with 10 g K2CO3 and stirred 1 hour, filtered and evaporated to dryness yielding a yellow-brown oily solid. The product was triturated with petroleum ether, decanted and evaporated to yield 13.8 g of the title compound (48%) as white-yellow crystals, mp=122° C., which can be recrystalized from a small amount of petroleum ether.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationwere filtered with suction
  4. washwashed with 0.5 L ether
  5. additionThe combined filtrates were treated with 10 g K2CO3
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customyielding a yellow-brown oily solid
  9. customThe product was triturated with petroleum ether
  10. customdecanted
  11. customevaporated

Sources & evidence

ORD record
ord-01fe1d99b4834909acb62e4ea42d621d
Source dataset
uspto-grants-1998_10
Patent number
US05827501

Reaction notes

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