Sodium Acetate → (2-Bromo-4,6-dichlorophenyl)methanol

HRID 648990Notes

Reaction equation

HRID 648990 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH2:4]Br.C([O-])(=[O:14])C.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH2:4][OH:14]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 104260681-Bromo-2-(bromomethyl)-3,5-dichlorobenzene

Product 1

HCID 14153164(2-Bromo-4,6-dichlorophenyl)methanolYield 56.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Heat a mixture of 22 g of 2-bromo-4,6-dichlorobenzyl bromide, 30 g anhydrous sodium acetate and 80 mL of glacial acetic acid for 18 hr at 100° C. Evaporate the mixture to a dry residue. Treat the residue with 200 mL of ethanol and 200 mL of 2N NaOH. Stir the mixture at reflux for 3 hr. Cool the mixture and concentrate the cooled mixture to 50 mL. Extract the cooled concentrate with Et2O. Dry the extract over anhydrous K2CO3 and evaporate it to a dry residue. Recrystallize the residue from toluene-hexane to give 10 g of 2-bromo-4,6-dichlorobenzyl alcohol, mp 111°-112° C.

Workup

  1. temperatureHeat
  2. customEvaporate the mixture to a dry residue
  3. additionTreat the residue with 200 mL of ethanol and 200 mL of 2N NaOH
  4. temperatureat reflux for 3 hr
  5. temperatureCool the mixture
  6. concentrationconcentrate the cooled mixture to 50 mL
  7. extractionExtract the cooled
  8. concentrationconcentrate with Et2O
  9. customDry the
  10. extractionextract over anhydrous K2CO3
  11. customevaporate it to a dry residue
  12. customRecrystallize the residue from toluene-hexane

Sources & evidence

ORD record
ord-aa0d6bdf782345bfa395dd76d5c9ce86
Source dataset
uspto-grants-1988_04
Patent number
US04737508

Reaction notes

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