Hydrochloric Acid → HCID 20138292, compound

HRID 1253037Notes

Reaction equation

HRID 1253037 reaction equation
[CH:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][Mg]Cl)=[CH:10][CH:9]=1.Cl>CCOCC>[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][CH:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12417PivalaldehydeHCID 178478997HCID 178478997, compound

Product 1

HCID 20138292HCID 20138292, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 10 ml quantity of ether solution of 4.3 g of (0.05 mole) of pivalaldehyde was added dropwise to a solution of p-chlorobenzylmagnesium chloride (0.055 mole) in 100 ml of ether with cooling and stirring. The mixture was thereafter stirred at room temperature for 1 hour and then placed into 5% aqueous solution of hydrochloride acid containing pieces of ice. After separating off the oily layer, the aqueous layer was subjected to extraction with ether. The ethereal extract and the oily layer were combined together, washed with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and distilled to remove the solvent, affording 10.5 g of the above-identified desired compound in the form of a white solid.

Workup

  1. temperaturewith cooling
  2. stirringThe mixture was thereafter stirred at room temperature for 1 hour
  3. additioncontaining pieces of ice
  4. customAfter separating off the oily layer
  5. extractionthe aqueous layer was subjected to extraction with ether
  6. extractionThe ethereal extract
  7. washwashed with saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationdistilled
  10. customto remove the solvent

Sources & evidence

ORD record
ord-d3323f9370df4ddc95d120bf87cfc093
Source dataset
uspto-grants-1988_05
Patent number
US04746673

Reaction notes

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