Pivalaldehyde → HCID 21409396, compound

HRID 1606711Notes

Reaction equation

HRID 1606711 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.[Mg].O1CCOC1.[CH3:20][C:21]([CH3:25])([CH3:24])[CH:22]=[O:23]>O1CCCC1>[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([CH:22]([OH:23])[C:21]([CH3:25])([CH3:24])[CH3:20])=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1

Participants

6

Reactant 4

HCID 12417PivalaldehydeHCID 125861,3-DioxolaneHCID 6149202-(4-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 5462224Magnesium

Product 1

HCID 21409396HCID 21409396, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 250 milliliters of tetrahydrofuran, 118 grams of the above dioxolane is dissolved. One quarter of this solution is then added to 12 grams of magnesium previously washed with chloroform, and refluxed with tetrahydrofuran for 20 minutes; and this mixture is refluxed 4 hours to initiate reaction. Additional dioxolane solution is thereafter added to maintain the refluxing without further heating. After the addition has been completed, 35 grams of 2,2-dimethylpropanal is added and the mixture is refluxed for 2 hours. The reactants are allowed to stand overnight and then poured onto ice-cold ammonium chloride solution. Tetrahydrofuran is added and the two layers formed are allowed to separate. The solvent layer is decanted off and the aqueous layer is extracted twice with 100 milliliters of tetrahydrofuran which are decanted off and combined with the remaining solvent layer. The organic phase is dried over anhydrous magnesium sulphate, filtered and evaporated to dryness to yield a yellow oil which is distilled at 120° to 150°C. at 30M and recrystallized from pentane/ether to yield 2-methyl- 2-(4-[1-hydroxy-2,2-dimethylpropyl]-phenyl)-1,3-dioxolane (m.p. 75°-80°C.).

Workup

  1. washpreviously washed with chloroform
  2. temperaturerefluxed with tetrahydrofuran for 20 minutes
  3. temperatureand this mixture is refluxed 4 hours
  4. customreaction
  5. temperatureto maintain the refluxing without further heating
  6. additionAfter the addition
  7. temperaturethe mixture is refluxed for 2 hours
  8. additionpoured onto ice-cold ammonium chloride solution
  9. customthe two layers formed
  10. customto separate
  11. customThe solvent layer is decanted off
  12. extractionthe aqueous layer is extracted twice with 100 milliliters of tetrahydrofuran which
  13. customare decanted off
  14. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  15. filtrationfiltered
  16. customevaporated to dryness
  17. customto yield a yellow oil which
  18. distillationis distilled at 120° to 150°C. at 30M
  19. customrecrystallized from pentane/ether

Sources & evidence

ORD record
ord-8de5e7a95dd942dab828559b00ec2c73
Source dataset
uspto-grants-1976_04
Patent number
US03953525

Reaction notes

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