Hydrochloric Acid → 2-Chloro-1-(2,4-dihydroxyphenyl)ethan-1-one

HRID 2118094Notes

Reaction equation

HRID 2118094 reaction equation
[O:1]1CCO[CH2:3][CH2:2]1.Cl.[C:8]1([CH:15]=[CH:14][CH:13]=[C:11]([OH:12])[CH:10]=1)[OH:9].[Cl:16]CC#N>[Cl-].[Cl-].[Zn+2].O>[Cl:16][CH2:3][C:2]([C:13]1[CH:14]=[CH:15][C:8]([OH:9])=[CH:10][C:11]=1[OH:12])=[O:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 7856ChloroacetonitrileHCID 312751,4-Dioxane

Product 1

HCID 23846862-Chloro-1-(2,4-dihydroxyphenyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 962WaterSolvent3×

Conditions

Temperature
27 °C

Procedure

A 100L round bottomed flask (RBF) containing 34.0 L of 1,4-dioxane was charged with 5.0 kg of HCl gas through a subsurface line. Resorcinol (10.0 kg) was then added as a solid, followed by addition of solid ZnCl2 (6.20 kg). A slight exotherm from 21 to 29° C. occurred after the ZnCl2 addition. The mixture was cooled with an ice/water bath, and chloroacetonitrile (7.50 kg) was added in portions over 2 h while maintaining the temperature at <40° C. The reaction mixture was aged 9 h at room temperature, and then water (34 L) was charged over 0.5 h. An exotherm to 40° C. occurred at the beginning of the water addition, and the reaction eventually cooled to 27° C. by the end of the addition. The resulting slurry was aged for 11 h at room temperature. More water (14L) was added, and the slurry was cooled to 0° C. The slurry was filtered, washed with water (4×20L), and then dried under a fast flow of nitrogen. After 5 days of drying, the chloroketone 2 was isolated as a light pink solid.

Workup

  1. customfrom 21 to 29° C.
  2. temperatureThe mixture was cooled with an ice/water bath
  3. temperaturewhile maintaining the temperature at <40° C
  4. customthe reaction
  5. waitThe resulting slurry was aged for 11 h at room temperature
  6. temperaturethe slurry was cooled to 0° C
  7. filtrationThe slurry was filtered
  8. washwashed with water (4×20L)
  9. customdried under a fast flow of nitrogen
  10. customAfter 5 days of drying

Sources & evidence

ORD record
ord-71b7f5a1357047bd9ab080b2fbc88b7e
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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