Water → 4-(1-Propoxyethyl)benzoic acid

HRID 2426741Notes

Reaction equation

HRID 2426741 reaction equation
[OH:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1)[CH3:3].[CH2:14](I)[CH2:15][CH3:16].[H-].[Na+].O>CN(C=O)C>[CH2:14]([O:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH3:3])[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Product 1

HCID 144734334-(1-Propoxyethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-(1-hydroxyethyl)benzoate (2.0 g) dissolved in DMF (30 ml) was mixed with propyl iodide (3.8 g), and then sodium hydride (50% in oil, 0.53 g) was added. After the end of the exothermic reaction, the mixture was stirred for 1 hour and then water was cautiously added. It was extracted with ethyl acetate, and the organic phase was dried over sodium sulfate, filtered and concentrated. The residue was hydrolyzed by method P-a. This resulted in the product with the molecular weight of 208.26 (C12H16O3); MS (ESI): 209 (M+H+).

Workup

  1. customAfter the end of the exothermic reaction
  2. extractionIt was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis resulted in the product with the molecular weight of 208.26 (C12H16O3)

Sources & evidence

ORD record
ord-b3b01efd66464ac298f4adeeafa3b066
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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