Water → (alphaRS)-Cyano-3-benzoylbenzyl alcohol

HRID 1731567Notes

Reaction equation

HRID 1731567 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C-:18]#[N:19].[Na+].S(=O)(=O)(O)O>O1CCOCC1>[C:18]([CH:12]([OH:13])[C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)#[N:19]

Participants

6

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 8929Sodium CyanideHCID 130201683-Benzoylbenzaldehyde

Product 1

HCID 12783740(alphaRS)-Cyano-3-benzoylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Benzoylbenzaldehyde (1.0 g) in dioxan (5 ml) was treated with water (2.5 ml) and sodium cyanide (0.5 g). The whole was cooled below 15° C. and 40% sulphuric acid (1.4 ml) added dropwise (care being taken to ensure that this temperature was not exceeded). Stirring was continued for 1 hour when water (30 ml) was added and the product extracted with methylene chloride and washed with water, saturated NaCl, dried over Na2SO4 and evaporated.

Workup

  1. temperatureThe whole was cooled below 15° C.
  2. extractionthe product extracted with methylene chloride
  3. washwashed with water, saturated NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-99bec91500e14a9382737df336d71050
Source dataset
uspto-grants-1986_11
Patent number
US04622337

Reaction notes

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