Ethanol → 2-Hydroxy-1-naphthaldehyde

HRID 613997Notes

Reaction equation

HRID 613997 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].CO.[CH2:14]([OH:16])C.C(Cl)(Cl)Cl>O.C(Cl)(Cl)Cl>[OH:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]=1[CH:14]=[O:16]

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 6212Chloroform4×HCID 86632-Naphthol

Product 1

HCID 128192-Hydroxy-1-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 6212ChloroformCatalystHCID 962WaterSolvent

Procedure

In step (a), β-naphthol is preferably first added to an aqueous alcoholic alkaline medium, for instance a solution of an alkali metal hydroxide in a mixture of water and a C1-C4 aliphatic alcohol, especially methanol or ethanol, at an elevated temperature preferably at a temperature within the range of 70°-100° C. To the resulting pale brown emulsion, the chloroform reactant is then added slowly -- preferably dropwise -- at an elevated temperature, preferably 70°-100° C. After the addition of a few drops of chloroform, the reaction mixture assumes a blue colouration which is allowed to change to green before any further chloroform is added. Subsequently, chloroform is added slowly and at such a rate that the green colouration is maintained. After completion of the addition of chloroform, the alkali metal salt of 2-hydroxy-1-naphthaldehyde may be isolated e.g. by filtration, and washed, preferably with brine.

Workup

  1. customwithin the range of 70°-100° C
  2. customat an elevated temperature, preferably 70°-100° C
  3. additionis added
  4. temperatureat such a rate that the green colouration is maintained

Sources & evidence

ORD record
ord-794d039d768b444aba21aff91d5daf14
Source dataset
uspto-grants-1979_03
Patent number
US04143058

Reaction notes

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