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

HRID 1648853Notes

Reaction equation

HRID 1648853 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>[OH:12][C:9]([C:8]1[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:7]=1[Cl:6])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:10][Cl:11]

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 low temperature condenser, a mechanical stirrer, an additional funnel and a nitrogen inlet tub, are placed 102 ml (0.2 m) of n-butyl lithium. This solution is cooled to -60° with an acetone-dry ice bath. A solution of 45 g (0.2 m) of 2,4-dichlorophenacyl chloride dissolved in 250 ml of dry ether is added dropwise. A constant flow of dry nitrogen is maintained throughout the addition. The rate of addition is adjusted so that the reaction temperature does not exceed -55°. After the addition, the reaction is gradually warmed to -10° and then poured into 500 ml of a mixture of saturated ammonium chloride solution and 10% hydrochloric acid solution. The organic layer is separated and the aqueous layer is further extracted with 100 ml of ether. The combined organic extracts are washed with 10% hydrochloric acid and dried over MgSO4. Solvent is evaporated to give 52 g of a pale yellow oil. This material is further purified by vacuum distillation (110°-120°/0.2 mm) to give 44 g of pure product.

Workup

  1. customInto a 500 ml four-necked flask equipped with a low temperature condenser, a mechanical stirrer, an additional funnel and a nitrogen inlet tub
  2. temperatureThis solution is cooled to -60° with an acetone-dry ice bath
  3. additionis added dropwise
  4. temperatureA constant flow of dry nitrogen is maintained throughout the addition
  5. additionThe rate of addition
  6. customdoes not exceed -55°
  7. additionAfter the addition
  8. temperaturethe reaction is gradually warmed to -10°
  9. customThe organic layer is separated
  10. extractionthe aqueous layer is further extracted with 100 ml of ether
  11. washThe combined organic extracts are washed with 10% hydrochloric acid
  12. dry with materialdried over MgSO4
  13. customSolvent is evaporated

Sources & evidence

ORD record
ord-bbf716e31182409f9595d19f066ef0dd
Source dataset
uspto-grants-1983_11
Patent number
US04414210

Reaction notes

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