Acetic Acid → 3-Phenoxybenzaldehyde

HRID 1679184Notes

Reaction equation

HRID 1679184 reaction equation
C1N2CN3CN(C2)CN1C3.[O:11]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=[O:28])C.Cl>O>[O:11]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=[O:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 932913-Phenoxybenzyl chloride

Product 1

HCID 382843-Phenoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hexamethylene tetramine (14.0 g) was added to a mixture of 3-phenoxybenzyl chloride (10.9 g), glacial acetic acid (25 ml) and water (25 ml) under a nitrogen atmosphere and the mixture refluxed for 2.5 hours, after which concentrated hydrochloric acid (20 ml) was added and the refluxing continued for a further 15 minutes. The mixture was cooled to the ambient temperature, extracted with diethyl ether and the extracts washed with water, saturated sodium bicarbonate solution, and finally with water. After drying the ethereal solution over anhydrous magnesium sulphate, the ether was evaporated under reduced pressure to yield 3-phenoxybenzaldehyde, identified by comparison with an authentic sample.

Workup

  1. temperaturethe mixture refluxed for 2.5 hours
  2. extractionextracted with diethyl ether
  3. washthe extracts washed with water, saturated sodium bicarbonate solution
  4. dry with materialAfter drying the ethereal solution over anhydrous magnesium sulphate
  5. customthe ether was evaporated under reduced pressure

Sources & evidence

ORD record
ord-deab38825d7140568e31c9ab4418dda9
Source dataset
uspto-grants-1978_03
Patent number
US04079182

Reaction notes

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