Benzyl Chloride → HCID 21517147, compound

HRID 1283961Notes

Reaction equation

HRID 1283961 reaction equation
[CH2:1]([O:8]C1C=C(C=CC=1OCCC)C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH2:32][CH3:33])[CH2:25][OH:26].C(Cl)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>C(O)C.O>[CH2:1]([O:8][C:23]1[CH:22]=[C:29]([O:30][CH2:31][CH2:32][CH3:33])[CH:28]=[CH:27][C:24]=1[CH:25]=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 214333893-(Benzyloxy)-4-propoxybenzaldehydeHCID 53777353HCID 53777353, compound

Product 1

HCID 21517147HCID 21517147, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

2,4,6-tribenzyloxyacetophenone is obtained by the common procedure of reacting 2,4,6-trihydroxyacetophenone with excess benzyl chloride and excess potassium carbonate in dimethylformamide and giving the reaction mixture an aqueous work up. 3-benzyloxy-4-n-propoxybenzaldehyde is similarly prepared from 3-hydroxy-4-n-propoxybenzyl alcohol, excess benzyl chloride and excess potassium carbonate. A warm solution of 2.19 g of the 2,4,6-tribenzyloxyacetophenone and 1.35 g of the benzyloxy-4-n-propoxybenzaldehyde is prepared in 10 ml of absolute ethanol. 15 Milliliters of warm aqueous 60% potassium hydroxide is added all at once. The mixture is stirred and a yellow solid product is formed. 16 Milliliters of absolute ethanol is added and the mixture is added to 300 ml of water and extracted three times with ethyl acetate. The extracts are dried and concentrated to yield 3.2 g of a solid, which is recrystallized to yield 2.6 g (75% yield) of 2,4,6,3'-tetrabenzyloxy-4'-n-propoxychalcone. ##SPC5## 1.38 Grams of this material is dissolved in about 50 ml of ethyl acetate and 200 mg of 5% palladium on charcoal is added. The reaction flask is flushed with hydrogen and then the mixture is stirred under hydrogen at room temperature for about 35 hours. The product is checked by thin layer chromatography and observed to contain essentially a single product. The reaction mixture is filtered and concentrated to yield 0.66 g of a colorless oil, which by NMR is determined to be 2,4,6,3'-tetrahydroxy-4'-n-propoxy dihydrochalcone, ##SPC6##

Workup

  1. customgiving the reaction mixture an aqueous work up
  2. customa yellow solid product is formed
  3. extractionextracted three times with ethyl acetate
  4. customThe extracts are dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c991a1762ae489eb753152c4804bdb0
Source dataset
uspto-grants-1976_08
Patent number
US03976790

Reaction notes

Loading…