3,4,5-Trimethoxybenzaldehyde → 3-(3,4,5-Trimethoxyphenyl)-2-propenal

HRID 1454006Notes

Reaction equation

HRID 1454006 reaction equation
BrC1C=C(C=CC=O)C=C(OC)C=1OC.COC1C=C(C=C(OC)C=1OC)C=O.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=[O:45])[CH:35]=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39].[CH3:46][O:47][C:48]1[CH:49]=[C:50]([OH:54])[CH:51]=[CH:52][CH:53]=1.N1CCOCC1>CO>[CH3:41][O:40][C:36]1[CH:35]=[C:34]([CH:42]=[CH:43][CH:44]=[O:45])[CH:33]=[C:32]([O:31][CH3:30])[C:37]=1[O:38][CH3:39].[CH3:46][O:47][C:48]1[CH:49]=[C:50]2[C:51]([CH:42]([C:34]3[CH:33]=[C:32]([O:31][CH3:30])[C:37]([O:38][CH3:39])=[C:36]([O:40][CH3:41])[CH:35]=3)[CH2:43][CH:44]([OH:45])[O:54]2)=[CH:52][CH:53]=1

Participants

8

Reactant 5

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 8083MorpholineHCID 90073-MethoxyphenolHCID 367983-(3,4,5-Trimethoxyphenyl)-2-propenalHCID 858878623-(3-Bromo-4,5-dimethoxyphenyl)-propenal

Product 2

HCID 367983-(3,4,5-Trimethoxyphenyl)-2-propenalHCID 575288747-Methoxy-2-hydroxy-4-(3,4,5-trimethoxy-phenyl)-chroman

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3,4,5-Trimethoxyphenyl)-propenal was prepared following the procedure for 3-(3-bromo-4,5-dimethoxyphenyl)-propenal as described in Example 15a using 3,4,5-trimethoxy benzaldehyde. 7-Methoxy-2-hydroxy-4-(3,4,5-trimethoxy-phenyl)-chroman was synthesized by the same procedure as Example 18 from 3-(3,4,5-trimethoxyphenyl)-propenal (71 mg; 0.32 mmol) and 3-methoxy phenol (43 mg; 0.35 mmol) using morpholine (30 μl) as a base in methanol (2.5 ml) (14 mg; 13%). 1H NMR (acetone-d6): 6.64 (dd, J=1.1, 8.5 Hz) and 6.59 (dd, J=1.0, 8.4 Hz) (1H), 6.54 (one doublet and one singlet overlapped, J=2.7 Hz; 2H), 6.38 (dd, J=2.6, 8.5 Hz; 1H), 6.34 (d overlapping with other small signals, J=2.3 Hz; 1H), 6.13 (d, J=6.8 Hz) and 6.08 (dd, J=1.0, 4.5 Hz) (1H), 5.62-5.65 and 5.47-5.51 (m each, 1H), 4.13-4.21 (overlapping dd, J=6.6, 10.2 Hz; 1H), 3.78, 3.77, 3.73, 3.72 (s each, 12H), 2.31 (ddd, J=2.1, 5.7, 13.1 Hz) and 2.08-2.13 (m) (2H).

Sources & evidence

ORD record
ord-02ebe571619b401fb3edf7adb2af3fec
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

Loading…