Hydrochloric Acid → 5-(Chloromethyl)-2-hydroxybenzaldehyde

HRID 903981Notes

Reaction equation

HRID 903981 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)O.[CH2:10]=[O:11].[ClH:12].[OH2:13]>>[CH:10]([C:7]1[CH:8]=[C:2]([CH:3]=[CH:5][C:6]=1[OH:13])[CH2:1][Cl:12])=[O:11]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 962WaterHCID 6998Salicylaldehyde

Product 1

HCID 3352915-(Chloromethyl)-2-hydroxybenzaldehydeYield 40%

Procedure

The compound was prepared by a modified procedure of Stoermer and Behn (R. Stoermer and K. Behn, Ber., 34 [1901], 2455). A 500-ml, three-neck flask equipped with a stirrer, thermometer and a gas inlet was charged with salicylaldehyde (61 g), formaldehyde (40 percent aqueous solution, 41 g) and hydrochloric acid (32 weight percent, 60 g). HCl gas was passed into the reaction mixture for 20 hours while the temperature was maintained below 30° C. The resulting dark purple reaction mixture was then treated with hot water (3×200 ml) to remove the unreacted paraformaldehyde. The crude product was sublimed at 100°/1 mm to give 34 g of white 3-formyl-4-hydroxybenzyl chloride (40 percent yield in salicylaldehyde), m.p. 90° C.

Workup

  1. customA 500-ml, three-neck flask equipped with a stirrer
  2. temperaturewas maintained below 30° C
  3. customto remove the unreacted paraformaldehyde
  4. customwas sublimed at 100°

Sources & evidence

ORD record
ord-d67b55ca9b454c038ae1a3b6b256acde
Source dataset
uspto-grants-1980_10
Patent number
US04229515

Reaction notes

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