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

HRID 1097907Notes

Reaction equation

HRID 1097907 reaction equation
C[O:2][C:3](=O)[CH:4]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[Cl:14])[CH3:5].[H-].C([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:14][C:7]1[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=1[CH:4]([CH3:5])[CH:3]=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 574213402-(2-Chloro-5-methoxy-phenyl)-propionic acid methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(2-Chloro-5-methoxy-phenyl)-propionic 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 and then 1 N potassium sodium tartrate solution (10 mL). The cooling bath was removed and the mixture was allowed to warm to RT. 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 (710 mg) and was used without further purification. 1H-NMR (□, 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 RT
  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-4544ed70255a4396a4956c8154263480
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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