Hydrochloric Acid → HCID 19767596, compound

HRID 1590592Notes

Reaction equation

HRID 1590592 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([OH:15])[CH2:13][OH:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.Cl>C1C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[C:19]([CH:20]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=3)[CH2:11][CH:12]([CH2:13][OH:14])[O:15]2)[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 114773-ChlorobenzaldehydeHCID 1178043-(3,4-Dimethoxyphenyl)propane-1,2-diol

Product 1

HCID 19767596HCID 19767596, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

15.64 g (73.6 mmoles) of dl-3-(3,4-dimethoxyphenyl)-propane-1,2-diol (II) are dissolved in 200 ml of benzene. 8.03 ml (73.6 mmoles) of 3-chlorobenzaldehyde and 4.6 ml (56 mmoles) of concentrated hydrochloric acid are added to the solution and the reaction mixture is stirred for 5 hours at room temperature. The solution is then evaporated in vacuo, the oily residue is dissolved in 200 ml of 99.5% ethanol, clarified while hot, filtered and the filtrate is evaporated in vacuo. Thus 23.19 g (94%) of crude product are obtained in oily form, which can be used for the further reaction steps without purification (the purity of the product exceeds 95%).

Workup

  1. customThe solution is then evaporated in vacuo
  2. dissolutionthe oily residue is dissolved in 200 ml of 99.5% ethanol
  3. filtrationfiltered
  4. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-fe4e541c470a43f0a67efe2cc0c633b5
Source dataset
uspto-grants-1993_04
Patent number
US05204343

Reaction notes

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