Hydrochloric Acid → 2-Hydroxy-2,4-dichlorophenethyl chloride

HRID 1648854Notes

Reaction equation

HRID 1648854 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4](=O)[CH2:5][Cl:6].[BH4-].[Na+].Cl.[O:16]1CCOCC1>O>[OH:16][C:2]1([Cl:1])[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][CH:3]1[CH2:4][CH2:5][Cl:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 202502,2',4'-TrichloroacetophenoneHCID 312751,4-DioxaneHCID 4311764Sodium borohydride2×

Product 1

HCID 204809262-Hydroxy-2,4-dichlorophenethyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 52 g (0.23 m) of 2,4-dichlorophenacyl chloride in 200 ml of dioxane is added 9 g (0.24 m) of sodium borohydride dissolved in 60 ml of water dropwise at 50°. The addition is set at such a rate that the reaction temperature does not exceed 50°. After the addition, the reaction mixture is stirred at 50° for 11/2 hours. Excess sodium borohydride is carefully decomposed by slow addition of 10% hydrochloric acid. The organic product is extracted into ether and the combined ether extracts are washed with water, saturated sodium bicarbonate solution, and dried over MgSO4. Solvent is evaporated to give 49 g of product.

Workup

  1. additionThe addition
  2. customdoes not exceed 50°
  3. additionAfter the addition
  4. extractionThe organic product is extracted into ether
  5. washthe combined ether extracts are washed with water, saturated sodium bicarbonate solution
  6. dry with materialdried over MgSO4
  7. customSolvent is evaporated

Sources & evidence

ORD record
ord-3b15a04a550c492d9fb066297dfcea73
Source dataset
uspto-grants-1983_11
Patent number
US04414210

Reaction notes

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