Hydrochloric Acid → HCID 20222006, compound

HRID 980080Notes

Reaction equation

HRID 980080 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:14])[CH2:10][CH2:11][CH:12]=[O:13].[CH3:15][Mg]I.Cl>C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:10][CH2:11][CH:12]([OH:13])[CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20222015HCID 20222015, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 20222006HCID 20222006, compoundYield 315.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4-(2,4-dichlorophenyl)pent-4-enal (26.0 g) in dry diethyl ether was added dropwise to a stirred solution of methylmagnesium iodide [from magnesium (4.09 g) and methyl iodide (24.14 g)] in diethyl ether (total volume of diethyl ether ca. 200 ml). Following the addition, the reaction mixture was stirred at room temperature for 1 hour then poured into a mixture of ice and dilute hydrochloric acid, and extracted with ether. The extracts were washed with water, dried over magnesium sulphate, concentrated under reduced pressure, and chromatographed on a column of silica gel (eluting with dichloromethane: 60°-80° petrol, 1:1) to give 2-(2,4-dichlorophenyl)hexan-5-ol (19.2 g, 69%) as an almost colourless oil.

Workup

  1. additionthe addition
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on a column of silica gel (eluting with dichloromethane: 60°-80° petrol, 1:1)

Sources & evidence

ORD record
ord-4318c52621a94f229d8e121f8e68b289
Source dataset
uspto-grants-1987_01
Patent number
US04636247

Reaction notes

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