Hydrochloric Acid → 3-(Phenylmethyl)salicylaldehyde

HRID 489140

Reaction equation

HRID 489140 reaction equation
[OH-:1].[Na+].[CH:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[CH:17](Cl)(Cl)Cl.Cl>O.C(O)C>[C:6]1([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([CH:17]=[O:1])[C:15]=2[OH:16])[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 242162-Benzylphenol

Product 1

HCID 222635343-(Phenylmethyl)salicylaldehydeYield 24%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

To a warm, stirred mixture of sodium hydroxide (8.0 g) in water (8.00 ml) was added a warmed solution of 2-hydroxydiphenylmethane (1), (4.9 g, 27 mmol) in ethanol (4 ml) and the mixture heated to 65° C. Chloroform (4.1 ml) was added down a water condensor and the resulting mixture began to reflux. After 1 h at reflux, the mixture was cooled in ice, acidified to pH 2 with 1N HCl and extracted with ethyl acetate (3×30 ml). The combined extracts were dried (Na2SO4) and the solvent removed to yield a dark brown gum. The product was eluted through a silica column, using 0-10% ethyl acetate in petroleum spirit to yield a yellow oil (1.33 g, 24%)

Workup

  1. temperatureto reflux
  2. temperatureAfter 1 h at reflux
  3. temperaturethe mixture was cooled in ice
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customthe solvent removed
  7. customto yield a dark brown gum
  8. washThe product was eluted through a silica column

Sources & evidence

ORD record
ord-c18fc22f121b49ff8c29557cd25da627
Source dataset
uspto-grants-2005_12
Patent number
US06977255B2

Linked notes

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