4-Hydroxybenzaldehyde → 4-(2-phenylethoxy)benzaldehyde

HRID 973394Notes

Reaction equation

HRID 973394 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.CN(C)C=O.Cl[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:16]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2314961-Chloro-2-phenylethane

Product 1

HCID 50620744-(2-phenylethoxy)benzaldehydeYield 50.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.2 g of 4-hydroxybenzaldehyde is mixed with 35 ml of dimethylformamide, 16.9 g of (2-chloroethyl)benzene and 16.6 g of potassium carbonate. The resulting mixture is stirred in a stream of nitrogen at 80°-90° C. for 10 hours and then cooled. The cooled mixture is added to 500 ml of water and then extracted with 500 ml of chloroform. The extract is washed with water until it becomes neutral. The washed extract is dried with anhydrous sodium sulfate and then chloroform is distilled away. The resulting residue is distilled under reduced pressure to obtain 11.4 g of 4-phenethyloxybenzaldehyde. Thus obtained 4-phenethyloxybenzaldehyde has a boiling point of 173°-181° C./2-3 mmHg.

Workup

  1. temperaturecooled
  2. extractionextracted with 500 ml of chloroform
  3. washThe extract is washed with water until it
  4. extractionThe washed extract
  5. dry with materialis dried with anhydrous sodium sulfate
  6. distillationchloroform is distilled away
  7. distillationThe resulting residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-47a2ac2452664095b3bc718f903df163
Source dataset
uspto-grants-1991_11
Patent number
US05063197

Reaction notes

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