3,4-Dichlorobenzaldehyde → (E)-4-(3,4-dichlorophenyl)-1-(3-methoxyphenyl)but-3-en-2-one

HRID 556156Notes

Reaction equation

HRID 556156 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH:17]=O>>[Cl:13][C:14]1[CH:15]=[C:16](/[CH:17]=[CH:11]/[C:10](=[O:12])[CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

3

Reactant 2

HCID 227103,4-DichlorobenzaldehydeHCID 764101-(3-Methoxyphenyl)acetone

Product 1

HCID 58950747(E)-4-(3,4-dichlorophenyl)-1-(3-methoxyphenyl)but-3-en-2-oneYield 36%

Procedure

The title compound was prepared in 36% yield from 1-(3-methoxyphenyl)propan-2-one and 3,4-dichlorobenzaldehyde following the procedure outlined in Example 9.1 above. 1H NMR (CDCl3, δ): 7.56 (d, J=2.0 Hz, 1H) 7.48 (d, J=16.0 Hz, 1H), 7.42 (d, J=8.3 Hz, 1H), 7.3 (m, 2H), 6.8(m, 3H), 6.73 (d, J=16.0 Hz, 1H), 3.88 (s, 2H), 3.79 (s, 3H). 13C NMR (CDCl3, δ): 196.5, 159.8, 140.4, 135.3, 134.4, 134.3, 133.1, 130.8, 129.8, 129.7, 127.3, 126.2, 121.7, 115.1, 112.5, 55.1, 48.7.

Sources & evidence

ORD record
ord-433e9802c7864549a493735e81a63894
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

Loading…