3,5-Dimethoxybenzaldehyde → Bis(3,5-dimethoxyphenyl)methanol

HRID 883826Notes

Reaction equation

HRID 883826 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=[O:7].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([Mg]Cl)[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1>C1COCC1>[CH3:12][O:11][C:9]1[CH:8]=[C:5]([CH:6]([C:17]2[CH:16]=[C:15]([O:14][CH3:13])[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=2)[OH:7])[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

4

Reactant 2

HCID 817473,5-DimethoxybenzaldehydeHCID 178493478HCID 178493478, compound

Product 1

HCID 67173126Bis(3,5-dimethoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

3,5-Dimethoxybenzaldehyde (5.0 g, 30 mmol) was dissolved in 150 mL THF in a 500 mL round bottom flask. 3,5-Dimethoxyphenyl magnesium chloride (1 M in THF, 45 mL) was added slowly. The reaction was heated at 40° C. for 4 hours, then quenched with saturated ammonium chloride. The mixture was extracted with 3 portions of ether and the combined organic layers washed with brine, dried over anhydrous MgSO4, then concentrated to a crude pale yellow solid which was carried forward to the next step.: 1H NMR (250 MHz, C6D6): δ 3.29 (d, J=5.0 Hz, 12H), 6.46 (m, 2H), 6.56 (m, 1H), 6.76 (m, 2H), 7.04 (t, J=8.2 Hz, 1H).

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionThe mixture was extracted with 3 portions of ether
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated to a crude pale yellow solid which

Sources & evidence

ORD record
ord-9d4430f49a32462bbf424de486187627
Source dataset
uspto-grants-2012_08
Patent number
US08237003B2

Reaction notes

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