3,4-Dihydroxybenzaldehyde → HCID 54039882, compound

HRID 973446Notes

Reaction equation

HRID 973446 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14]C)[CH:6]=[CH:7][C:8]([OH:10])=[O:9].CO[C:18]1[CH:19]=[C:20]([CH2:26][CH2:27]CO)[CH:21]=[CH:22][C:23]=1[O:24]C.[C:30](CC(O)=O)#[N:31].B(Cl)(Cl)Cl.OC1C=C(C=CC=1O)C=O>>[C:30]([C:7](=[CH:6][C:5]1[CH:11]=[CH:12][C:13]([OH:14])=[C:3]([OH:2])[CH:4]=1)[C:8]([O:10][CH2:27][CH2:26][C:20]1[CH:21]=[CH:22][C:23]([OH:24])=[CH:18][CH:19]=1)=[O:9])#[N:31]

Participants

6

Reactant 5

HCID 87683,4-DihydroxybenzaldehydeHCID 9740Cyanoacetic acidHCID 168483',4'-Dimethoxycinnamic acidHCID 25135Boron TrichlorideHCID 775283-(3',4'-Dimethoxyphenyl)-1-propanol

Product 1

HCID 54039882HCID 54039882, compound

Procedure

After the reduction of 3,4-dimethoxycinnamic acid to 3-(3,4-dimethoxyphenyl)propanol in the usual manner followed by condensation with cyanoacetic acid according to the procedure in Example 3, the product was demethylated with boron trichloride and condensed with 3,4-dihydroxybenzaldehyde to give the following compound.

Workup

  1. customto give the following compound

Sources & evidence

ORD record
ord-e8db239b42e44e63874fdb8a7a81064e
Source dataset
uspto-grants-1991_11
Patent number
US05063243

Reaction notes

Loading…