Ethanol → 4-Hydroxybenzaldehyde

HRID 1703412Notes

Reaction equation

HRID 1703412 reaction equation
C(Cl)(Cl)Cl.[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].[CH2:14]([OH:16])C>>[CH:14](=[O:16])[C:6]1[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:11].[OH:11][C:5]1[CH:10]=[CH:9][C:8]([CH:14]=[O:16])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 996PhenolHCID 6212Chloroform2×HCID 14798Sodium Hydroxide

Product 2

HCID 1264-HydroxybenzaldehydeHCID 6998Salicylaldehyde

Procedure

Sen et al J. Indian Chem. Soc. 9 173 (1932) state that the use of chloroform in an ethyl alcohol solution in the Reimer-Tiemann reaction increases the yield of aldehyde. However, the only example describing the reaction of phenol with chloroform and sodium hydroxide in aqueous ethyl alcohol shows a combined yield for salicylaldehyde and p-hydroxybenzaldehyde of only 33%, based on the phenol reacted. The proportion of salicylaldehyde to p-hydroxybenzaldehyde in the product is about five to one, the same as for the conventional aqueous reaction.

Sources & evidence

ORD record
ord-7fc6fb7987b64c39b04f5870873d42c4
Source dataset
uspto-grants-1982_09
Patent number
US04351962

Reaction notes

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