N-Benzylideneaniline → 6-Methoxy-2-[4-(2-phenylethenyl)phenyl]-1-benzofuran

HRID 1730636Notes

Reaction equation

[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:10]=3[CH:11]=2)=[CH:3][CH:2]=1.[CH:19](=NC1C=CC=CC=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:1]1([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:2]=[CH:3][C:4]([C:7]2[O:8][C:9]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:10]=3[CH:11]=2)=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 10858N-Benzylideneaniline

HCID 189255446-Methoxy-2-(4-methylphenyl)-1-benzofuran

Product 1

HCID 537467886-Methoxy-2-[4-(2-phenylethenyl)phenyl]-1-benzofuran

Procedure

Following the procedure given in Example 1b 2-(p-tolyl)-6-methoxybenzofuran was interacted with an equimolar quantity or benzalaniline to produce 2-(4-stilbenyl)-6-methoxybenzofuran, which, when recrystallized from toluene, melted at 223.5°-225.5° C. The wavelength of maximum excitation of this compound was 371 nm., and the wavelength of maximum emission was 446 nm.

Sources & evidence

ORD record: ord-0a1bbb0cf2b84648b1461b52e15fd399
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03993645

Reaction notes

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