Hydrochloric Acid → 1-Chloro-2-(2,4-dichlorophenyl)hexan-2-ol

HRID 1648751Notes

Reaction equation

HRID 1648751 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Cl:6][C:7]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:8]=1[C:9](=[O:12])[CH2:10][Cl:11].[Cl-].[NH4+].Cl>CCOCC>[Cl:11][CH2:10][C:9]([C:8]1[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:7]=1[Cl:6])([OH:12])[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 202502,2',4'-TrichloroacetophenoneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 132368981-Chloro-2-(2,4-dichlorophenyl)hexan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a 500 ml four-necked flask equipped with a thermometer, a condenser, a mechanical stirrer, an addition funnel, and a nitrogen inlet tube are placed 102 ml (0.2 m, 1.97 M solution in hexane) of n-butyllithium. This solution is cooled to -60° with an acetone-dry ice bath. 2,4-Dichlorphenacyl chloride (44.7 g, 0.2 m) dissolved in 250 ml of ether is then added dropwise. The temperature is maintained below -55° throughout the reaction. After the addition, the reaction is allowed to warm gradually to -10° and then poured into a mixture containing 250 ml of saturated ammonium chloride and 250 ml of 10% hydrochloric acid solution. The layers are separated and the aqueous layer is extracted with 100 ml of ether. The combined ether extracts are washed with 10% hydrochloric acid, saturated sodium chloride solution, and dried over MgSO4. Solvent is evaporated to give 52 g of a pale yellow oil. Vacuum distillation (100°-120°/0.2 mm) affords 44 g of pure product.

Workup

  1. customInto a 500 ml four-necked flask equipped with a thermometer, a condenser, a mechanical stirrer, an addition funnel, and a nitrogen inlet tube
  2. temperatureThis solution is cooled to -60° with an acetone-dry ice bath
  3. additionis then added dropwise
  4. temperatureThe temperature is maintained below -55° throughout the reaction
  5. additionAfter the addition
  6. temperatureto warm gradually to -10°
  7. additionpoured into a mixture
  8. customThe layers are separated
  9. extractionthe aqueous layer is extracted with 100 ml of ether
  10. washThe combined ether extracts are washed with 10% hydrochloric acid, saturated sodium chloride solution
  11. dry with materialdried over MgSO4
  12. customSolvent is evaporated

Sources & evidence

ORD record
ord-95762904680449ffbfb12f3ea33258a6
Source dataset
uspto-grants-1983_11
Patent number
US04413003

Reaction notes

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