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

HRID 2378169Notes

Reaction equation

HRID 2378169 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].Br[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=1.C([Li])CCC.O1C2C=CC(C(C3C=C(OC)C=C(OC)C=3)O)=CC=2OCC1>>[CH3:12][O:11][C:9]1[CH:8]=[C:5]([CH:6]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=2)[OH:7])[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

5

Reactant 4

HCID 817473,5-DimethoxybenzaldehydeHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 69202534(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanolHCID 178418339Butyllithium

Product 1

HCID 67173126Bis(3,5-dimethoxyphenyl)methanolYield 86%

Procedure

3,5-Dimethoxybenzaldehyde (0.84 g, 5.03 mmol), 1-bromo-3,5-dimethoxybenzene (1.20 g, 5.53 mmol), and n-butyl lithium (2.20 ml, 5.53 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 60% EtOAc in hexane in about 40 min.) to give Bis-(3,5-dimethoxy-phenyl)-methanol as an off-white solid (1.31 g, 86%): 1HNMR (CDCl3) 6.55 (d, J=2 Hz, 4H, Ar), 6.36 (t, J=2 Hz, 2H, Ar), 5.67 (d, J=3 Hz, 1H, CHOH), 3.77 (s, 12H, 4OCH3), 2.24 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Workup

  1. customThe crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 60% EtOAc in hexane in about 40 min.)

Sources & evidence

ORD record
ord-75c10999b6894b5a9919e15d4b64429e
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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