4-Methylbenzaldehyde → (+/-)-3,3-Dimethyl-1-p-tolyl-butan-1-ol

HRID 911442Notes

Reaction equation

HRID 911442 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([Mg]Cl)[C:11]([CH3:14])([CH3:13])[CH3:12]>C1COCC1.[NH4+].[Cl-]>[CH3:10][C:11]([CH3:14])([CH3:13])[CH2:12][CH:6]([C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=1)[OH:7]

Participants

5

Reactant 2

HCID 77254-MethylbenzaldehydeHCID 178418809HCID 178418809, compound

Product 1

HCID 57656593(+/-)-3,3-Dimethyl-1-p-tolyl-butan-1-olYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-methylbenzaldehyde (1.51 g, 12.6 mmol) in THF (30 mL) at 0° C., add neopentyl magnesium chloride (33.0 mL, 16.34 mmol, 0.5-1M in ether) and continue stirring at 0° C. for 1 h. Dilute with saturated aqueous NH4Cl, extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (95:5) to give the desired intermediate as a colorless oil (2.15 g, 89%).

Workup

  1. extractionextract three times with EtOAc
  2. dry with materialdry over anhydrous Na2SO4
  3. concentrationconcentrate in vacuo
  4. customPurify by chromatography on silica gel eluting with hexane/EtOAc (95:5)

Sources & evidence

ORD record
ord-13f4548ed41b4119bba0c9467dcd5af9
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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