2,3-Dimethoxybenzaldehyde → HCID 69203248, compound

HRID 2378185Notes

Reaction equation

HRID 2378185 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].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>>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=1)[OH:6]

Participants

5

Reactant 4

HCID 665812,3-DimethoxybenzaldehydeHCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 69202534(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanolHCID 178418339Butyllithium

Product 1

HCID 69203248HCID 69203248, compoundYield 89%

Procedure

2,3-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 50% EtOAc in hexane in about 40 min.) to give (2,3-dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanol as a greenish yellow oil (1.36 g, 89%): 1HNMR (CDCl3) 7.08-7.01 (m, 1H, Ar), 6.93-6.85 (m, 2H, Ar), 6.57 (d, J=2 Hz, 2H, Ar), 6.35 (t, J=2 Hz, 1H, Ar), 5.94 (d, J=6 Hz, 1H, CHOH), 3.86 (s, 3H, OCH3), 3.76 (s, 6H, 2OCH3), 3.66 (s, 3H, OCH3), 3.05 (d, J=6 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 50% EtOAc in hexane in about 40 min.)

Sources & evidence

ORD record
ord-231e7342b95f4538aaaa49a656b93ba2
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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