Acetic Acid → HCID 14520335, compound

HRID 1194363Notes

Reaction equation

HRID 1194363 reaction equation
S(=O)(=O)(O)O.[CH2:6]=O.[Br:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[OH:16].[OH-].[Na+].[C:19]([OH:22])(=O)C>>[Br:8][C:9]1[C:10]2[O:16][CH2:6][O:22][CH2:19][C:11]=2[CH:12]=[C:13]([Cl:15])[CH:14]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 696702-Bromo-4-chlorophenol

Product 1

HCID 14520335HCID 14520335, compoundYield 65.5%

Conditions

Temperature
15 °C

Procedure

Into a mixture of 229 ml of concentrated sulfuric acid and 620 ml of acetic acid, cooled to 15° C. there is added all at once 311 g of paraformaldehyde (previously washed with 200 ml of acetic acid), followed by 462.6 g (2.23 moles) of 2-bromo-4-chlorophenol. The reaction mixture is stirred for 148 hours at 15° C. It is then neutralized with 3.1 liters of a 7.8N aqueous solution of sodium hydroxide. The precipitate formed is filtered off, dried and then dissolved in toluene. The solution is dried over anhydrous sodium sulfate and then distilled. The residue is stirred in hexane and allowed to crystallize. 364 g of 8-bromo-6-chloro-4H-1,3-benzodioxin are obtained. Yield: 65.5% of theory; M.P.: 108°-110° C.

Workup

  1. washpreviously washed with 200 ml of acetic acid),
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. customdried
  5. dissolutiondissolved in toluene
  6. dry with materialThe solution is dried over anhydrous sodium sulfate
  7. distillationdistilled
  8. stirringThe residue is stirred in hexane
  9. customto crystallize

Sources & evidence

ORD record
ord-cbfa0dc9a3304400b9c30a941ee18ca8
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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