Water → 3-Phenoxybenzaldehyde

HRID 1659655Notes

Reaction equation

HRID 1659655 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]2OCC[O:15]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C-]#N.[Na+].O>C1(C)C(C)=CC=CC=1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH:14]=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 1118Sulfuric Acid2×HCID 8929Sodium CyanideHCID 136438312-(3-Phenoxyphenyl)-1,3-dioxolane

Product 1

HCID 382843-PhenoxybenzaldehydeYield 58%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 7237O-XyleneSolvent2×

Procedure

A solution of 2-(3-phenoxyphenyl)-1,3-dioxolane prepared according to Example 7 in xylene is treated with an aqueous sulfuric acid solution as described in Example 8. The reaction mixture is cooled and 83 g. of tetrabutylammonium chloride are added followed by a dropwise addition of a solution of 100 g. of sodium cyanide in 500 ml. of water at 10° to 20° C. Thereafter a solution of 48 ml. of concentrated sulfuric acid in 500 ml. of water is added dropwise and the reaction mixture is stirred until no traces of starting compound can be detected by thin layer chromatography. From the xylene phase 196 g. of 3-phenoxybenzaldehyde cyanehydrin are isolated. The purity of the product obtained is better than 95% (determined by NMR spectroscopy). Yield: 58% calculated for 2-(3-chlorophenyl)-1,3-dioxolane.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionfollowed by a dropwise addition of a solution of 100 g
  3. customat 10° to 20° C

Sources & evidence

ORD record
ord-a2027a301e7a45b6827a6d8cc4e9edb0
Source dataset
uspto-grants-1981_12
Patent number
US04304938

Reaction notes

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