Dimethylformamide → 3-Phenoxybenzaldehyde

HRID 1659656Notes

Reaction equation

HRID 1659656 reaction equation
CN(C)C=O.S(=O)(O)O.[O:10]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C-]#N.[Na+]>C(OC(=O)C)C.O.C(O)(=O)C>[O:10]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 205556583-Phenoxybenzaldehyde bisulfite

Product 1

HCID 382843-Phenoxybenzaldehyde

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Into 150 ml. of dimethyl formamide 60.45 g. of 3-phenoxybenzaldehyde bisulfite are added, whereupon a solution of 12.51 g. of sodium cyanide in 60 ml. of water is poured into the mixture at 5° to 10° C. under cooling with ice water, in 25 to 35 minutes. The mixture is stirred to 10° to 12° C. for 1 hour and 62 ml. of acetic acid are added at 10° to 15° C., dropwise, in 25 to 30 minutes. The reaction mixture is stirred for an additional 20 minutes, whereupon it is poured into a vigurously stirred mixture of 500 ml. of water and 300 ml. of ethylacetate. From the organic phase 44 g. of 3-phenoxybenzaldehyde cyanehydrin are isolated. The purity of the product obtained is better than 95% (determined by NMR spectroscopy).

Workup

  1. waitdropwise, in 25 to 30 minutes
  2. stirringThe reaction mixture is stirred for an additional 20 minutes, whereupon it
  3. additionis poured into a vigurously stirred mixture of 500 ml

Sources & evidence

ORD record
ord-ecc0128734134abaa159d76e9994d996
Source dataset
uspto-grants-1981_12
Patent number
US04304938

Reaction notes

Loading…