Methanol → 1-(4-chlorophenyl)-1,3-Propanediol

HRID 1289412Notes

Reaction equation

HRID 1289412 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)C.[H-].C([Al+]C(C)C)(C)C.CO.O>C(Cl)Cl>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]([OH:14])[CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 101336Ethyl 3-(4-chlorophenyl)-3-oxopropanoateHCID 21896610Diisopropylaluminium hydride

Product 1

HCID 103300821-(4-chlorophenyl)-1,3-PropanediolYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g of ethyl-4-chlorobenzoylacetate in 100 ml of methylene chloride cooled to -30° C., 77.3 ml of diisopropylaluminium hydride (1.0 mol/l toluene solution) was added, and the resulting mixture was stirred for 30 minutes and then brought back to room temperature over 3 hours, and 4.14 g of methanol and 24.3 g of water were added carefully, and the mixture was stirred for another 1.5 hours. The precipitate was filtered off, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=1/1), to obtain 2.45 g of the title compound as a pale yellow oily substance.

Workup

  1. waitbrought back to room temperature over 3 hours
  2. stirringthe mixture was stirred for another 1.5 hours
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4674923391614f98b446baaf4fea5ad9
Source dataset
uspto-grants-1998_05
Patent number
US05750523

Reaction notes

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