Hydrochloric Acid → 2-(2,4-Dichlorophenoxy)propan-1-ol

HRID 1031865Notes

Reaction equation

HRID 1031865 reaction equation
B.[Cl:2][C:3]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:4]=1[O:5][CH:6]([CH3:10])[C:7](O)=[O:8].Cl>O1CCCC1.CO>[Cl:2][C:3]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:4]=1[O:5][CH:6]([CH3:10])[CH2:7][OH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 8427Dichlorprop

Product 1

HCID 3509832-(2,4-Dichlorophenoxy)propan-1-olYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

43 ml of a 1 M solution of borane in tetrahydrofuran (THF) were stirred under nitrogen and cooled in ice while a solution of 6.8 g of 2-(2,4-dichlorophenoxy)propionic acid in 40 ml of THF was added dropwise thereto. The mixture was heated to boiling under reflux for 1 hour and then cooled to room temperature. 22 ml of a saturated solution of hydrogen chloride in methanol were added dropwise and the solution was heated to boiling under reflux for 1 hour. The mixture was evaporated and the residue was treated with 22 ml of a saturated solution of hydrogen chloride in methanol. After heating under reflux for 1 hour the mixture was evaporated and the residue was partitioned between 100 ml of saturated sodium bicarbonate solution and 100 ml of methylene chloride. The layers were separated and the aqueous layer was extracted with 100 ml of methylene chloride. The combined organic extracts were dried over sodium sulphate and evaporated to give 6.4 g of 2-(2,4-dichlorophenoxy)-propanol as a yellow oil.

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperaturethe solution was heated
  5. temperatureunder reflux for 1 hour
  6. customThe mixture was evaporated
  7. additionthe residue was treated with 22 ml of a saturated solution of hydrogen chloride in methanol
  8. temperatureAfter heating
  9. temperatureunder reflux for 1 hour the mixture
  10. customwas evaporated
  11. customthe residue was partitioned between 100 ml of saturated sodium bicarbonate solution and 100 ml of methylene chloride
  12. customThe layers were separated
  13. extractionthe aqueous layer was extracted with 100 ml of methylene chloride
  14. dry with materialThe combined organic extracts were dried over sodium sulphate
  15. customevaporated

Sources & evidence

ORD record
ord-6f7accd342e845e395bd2972a3a6ef06
Source dataset
uspto-grants-1990_09
Patent number
US04956346

Reaction notes

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