Ammonia → 3-Phenoxybenzaldehyde

HRID 2083273Notes

Reaction equation

HRID 2083273 reaction equation
C=O.N.[O:4]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14]Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[O:19](C1C=C(C=CC=1)C(Cl)Cl)C1C=CC=CC=1>C(O)(=O)C>[O:4]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 932913-Phenoxybenzyl chlorideHCID 1046311-(Dichloromethyl)-3-phenoxybenzene

Product 1

HCID 382843-Phenoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of formalin (40%, 150 ml) was cooled to 10° C and then treated with aqueous ammonia solution (35%, 75 ml) over 15 minutes. A mixture of 3-phenoxybenzyl chloride and 3-phenoxybenzal chloride containing 70% monochloride chloride and 30% dichloride mixture (50 g) was added and the mixture stirred under a nitrogen blanket for 3 hours. The mixture was then acidified with acetic acid (150 ml), stirred for a further 3 hours in the cold, and then refluxed for 4 hours. After cooling, the reaction mixture was extracted with toluene (100 ml) and the extract washed neutral with sodium bicarbonate solution. The toluene solution of crude 3-phenoxybenzaldehyde was diluted with an equal quantity of ethanol and then stirred with a saturated aqueous solution of sodium bisulphite. The resulting bisulphite adduct was filtered off and washed with toluene. After vacuum drying, this gave 63.0 g of purified 3-phenoxybenzaldehyde bisulphite compound which on treatment with dilute mineral acid yielded the pure 3-phenoxybenzaldehyde. Yield based on chloride mixture was 95%.

Workup

  1. additionwas added
  2. stirringstirred for a further 3 hours in the cold, and
  3. temperaturethen refluxed for 4 hours
  4. temperatureAfter cooling
  5. extractionthe reaction mixture was extracted with toluene (100 ml)
  6. washthe extract washed neutral with sodium bicarbonate solution
  7. additionThe toluene solution of crude 3-phenoxybenzaldehyde was diluted with an equal quantity of ethanol
  8. stirringstirred with a saturated aqueous solution of sodium bisulphite
  9. filtrationThe resulting bisulphite adduct was filtered off
  10. washwashed with toluene
  11. customAfter vacuum drying
  12. additionthis gave 63.0 g of purified 3-phenoxybenzaldehyde bisulphite compound which on treatment with dilute mineral acid

Sources & evidence

ORD record
ord-12901585428f427b8d9aa4c48d1bf5dd
Source dataset
uspto-grants-1978_04
Patent number
US04085147

Reaction notes

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