Water → Dibenzyl

HRID 1605201Notes

Reaction equation

HRID 1605201 reaction equation
C[C:2]1[C:7]([CH:8]=O)=[CH:6][C:5](OC)=[C:4](OC)[CH:3]=1.[CH2:14]([Mg]Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1COCC1>[C:15]1([CH2:14][CH2:8][C:7]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 821414,5-Dimethoxy-2-methylbenzaldehydeHCID 178418336HCID 178418336, compound

Product 1

HCID 7647Dibenzyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 10 g of 6-methylveratraldehyde under a nitrogen atmosphere in 75 ml dry THF was added dropwise 1.5 equivalents benzylmagnesium chloride in 20 ml dry THF. After stirring overnight at room temperature, 20 ml water was added. The residue remaining after most of the THF had been distilled off was added to an additional 100 ml water and extracted with ether to give a yellow oil. Distillation under reduced pressure gave bibenzyl resulting from coupling of the Grignard reagent and a quantitative yield of the adduct 12 as a colorless viscous oil, bp 170°-175°(0.05 mm Hg). Nmr (δ): 2.08 (s, 3H), 2.88 (distorted doublet, J - 6 cps, integration for 3 H suggests coincidence with the alcohol proton), 3.75 (s, 6H), 4.96 (t, J = 6 cps, 1H), 6.52 (s, 1H), 7.00 (s, 1H), 7.15 (s, 5H),. Anal. Calcd. for C17H 20 O3 : C, 74.97; H, 7.40. Found: C, 75.38; H, 7.43.

Workup

  1. distillationhad been distilled off
  2. additionwas added to an additional 100 ml water
  3. extractionextracted with ether
  4. customto give a yellow oil
  5. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-4fd030c9bb3e4cf89738a4d7742c8c28
Source dataset
uspto-grants-1976_04
Patent number
US03950236

Reaction notes

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