2,4-Dichlorobenzaldehyde → (2,4-Dichloro-phenyl)-3-methyl-butan-1-ol

HRID 1671325Notes

Reaction equation

HRID 1671325 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11]([Li])[CH:12]([CH3:14])[CH3:13].[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 134042,4-DichlorobenzaldehydeHCID 25517Ammonium ChlorideHCID 178506859HCID 178506859, compound

Product 1

HCID 61271586(2,4-Dichloro-phenyl)-3-methyl-butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) stirred solution of 2,4-dichlorobenzaldehyde (2 g, 11.43 mmol) in THF (50 ml) under N2 is added isobutyllithium (7.86 ml, 12.57 mmol) slowly and the reaction is stirred at RT over the weekend. The reaction mixture is added to sat. ammonium chloride (100 ml) and extracted with EtOAc (140 ml). The organic portion is washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by chromatography on silica (70 g/150 ml silica-column) eluting with 10% EtOAc/iso-hexane to give (2,4-dichloro-phenyl)-3-methyl-butan-1-ol as a yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.53 (1H, d, J 8.3), 7.36 (1H, d, J 2.0), 7.29 (1H, dd, J 8.3, 2.0), 5.18 (1H, dd, J 9.2, 3.7), 1.88 (1H, m), 1.61 (1H, ddd, 14.0, 9.2, 4.7), 1.52 (1H, ddd, 14.0, 9.1, 3.7), 1.03 (3H, d, J 6.6), 0.99 (3H, d, J 6.6).

Workup

  1. extractionextracted with EtOAc (140 ml)
  2. washThe organic portion is washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by chromatography on silica (70 g/150 ml silica-column)
  6. washeluting with 10% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-304aa0e1967a45849f03d7075992d09e
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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