3-Methoxybenzaldehyde → HCID 12197872, compound

HRID 971023Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1.C([Li])CCC.COC1C=C(C(C2C=CC=C(OC)C=2)=CC#N)C=C(OC)C=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[OH:7])[CH:8]=[CH:9][CH:10]=1

Participants

Reactant 4

HCID 115693-Methoxybenzaldehyde

HCID 169713-Bromoanisole

HCID 692052993-(3,5-Dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile

HCID 178418339Butyllithium

Product 1

HCID 12197872HCID 12197872, compoundYield 100.8%

Procedure

3-methoxybenzaldehyde (2.20 ml, 18.08 mmol), 1-bromo-3-methoxybenzene (2.52 ml, 19.89 mmol), and n-butyl lithium (7.96 ml, 19.89 mmol) were treated in the same manner as described above for the synthesis of 3-(3,5-dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile. The crude was purified via flash column chromatography (10% EtOAc in hexane gradient to 25% EtOAc in hexane in about 40 min.) to give bis-(3-methoxy-phenyl)-methanol as a light yellow oil (4.45 g, 100%): 1HNMR (CDCl3) 7.28-7.21 (m, 2H, Ar), 6.96-6.94 (m, 4H, Ar), 6.82-6.78 (m, 2H, Ar), 5.78 (d, J=3 Hz, 1H, CHOH), 3.78 (s, 6H, 2OCH3 groups), 2.25 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Workup

customThe crude was purified via flash column chromatography (10% EtOAc in hexane gradient to 25% EtOAc in hexane in about 40 min.)

Sources & evidence

ORD record: ord-81f96c9e42ee467eb8e29786e2b70d69
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312241B2

Reaction notes

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