Methanol → 2-(2-Chloro-5-methoxy-phenyl)-propionaldehyde

HRID 1095948Notes

Reaction equation

HRID 1095948 reaction equation
CO[C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[Cl:13].[H-].[CH2:16]([Al+]CC(C)C)C(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Cl:13][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[CH:4]([CH3:16])[CH:3]=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 15576550Methyl 2-(2-chloro-5-methoxyphenyl)acetateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 574499712-(2-Chloro-5-methoxy-phenyl)-propionaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

2-Chloro-5-methoxy-benzeneacetic acid methyl ester (850 mg) was dissolved in toluene (40 mL) and cooled to −78° C. Diisobutylaluminium hydride (20% in toluene, 3.69 mL) was added over a period of 15 minutes. Stirring was continued for 45 minutes at −78° C. Methanol (2 mL) was added followed by 1M potassium sodium tartrate solution (10 mL). The cooling bath was removed and the mixture was allowed to warm to r.t. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The title compound was obtained as a light yellow oil (710mg, 96%) and was used without further purification. 1H-NMR (δ, CDCl3): 9.72 (s, 1H), 7.34 (d, 1H), 6.79 (dd, 1H), 6.66 (d, 1H), 4.10 (q, 1H), 3.79 (s, 3H), 1.43 (d, 3H).

Workup

  1. customThe cooling bath was removed
  2. temperatureto warm to r.t
  3. additionThe mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-1246e4b3d1ac42e99aafe7f1c3f03c5e
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

Loading…