4-Hydroxybenzaldehyde → HCID 53410019, compound

HRID 973395Notes

Reaction equation

HRID 973395 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](Cl)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:10]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 53410019HCID 53410019, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.4 g of 4-hydroxybenzaldehyde is mixed with 50 ml of dimethylformamide, 30.4 g of cinnamyl chloride and 30.4 g of potassium carbonate. The resulting mixture is stirred in a stream of nitrogen at 100°-110° C. for 5 hours and then cooled. The cooled mixture is added to 2 l of ice water to deposit solid. The solid is separated therefrom by filtration and then washed with water until the solid becomes neutral. The washed solid is dried and then recrystallized from 200 ml of ethanol to obtain 36.4 g of 4-cinnamyloxybenzaldehyde. Thus obtained 4-cinnamyloxybenzaldehyde has a melting point of 89.5°-90.5° C.

Workup

  1. temperaturecooled
  2. customThe solid is separated
  3. filtrationby filtration
  4. washwashed with water until the solid
  5. customThe washed solid is dried
  6. customrecrystallized from 200 ml of ethanol

Sources & evidence

ORD record
ord-8f2682428e434af6be903a0d35f516e1
Source dataset
uspto-grants-1991_11
Patent number
US05063197

Reaction notes

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