Hydrochloric Acid → 5-Chloro-salicylaldehyde

HRID 1982179Notes

Reaction equation

HRID 1982179 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CCCCCCCC)CCCCCCCC)CCCCCCC.[Sn](Cl)(Cl)(Cl)Cl.[CH2:39]=[O:40].Cl>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[C:6]([CH:39]=[O:40])[C:5]([OH:8])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 46844-ChlorophenolHCID 14227TrioctylamineHCID 24287Tin tetrachloride

Product 1

HCID 124815-Chloro-salicylaldehydeYield 30.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

64.25 g (0.5 mole) of p-chlorophenol and 55 g (0.2 mole) of trioctylamine are dissolved in 100 ml of toluene. Under N2, 13 g of tin tetrachloride are added dropwise at 0° C. After 20 min at room temperature, 33 g of dried paraformaldehyde are added, and the mixture is heated at 100° C. for 5 hours. After cooling, the mixture is poured onto 2.5 l of H2O, and the mixture is acidified to pH 2 with 2N HCl and extracted with diethyl ether. The ether phase is washed with saturated NaCl solution and dried with Na2SO4 and concentrated. Chromatography on silica gel using ethyl acetate/cyclohexane (1:6) provides 24 g of the title compound, melting point 99° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. washThe ether phase is washed with saturated NaCl solution
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bc8a473bf41f484b9fcbea8b92d9ea00
Source dataset
uspto-grants-1986_06
Patent number
US04595685

Reaction notes

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