1-Propanol → 4-(Propoxymethyl)benzoic acid

HRID 2426738Notes

Reaction equation

HRID 2426738 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][CH3:5].Br[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1>CN(C=O)C>[CH2:3]([O:6][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 176060524-(Propoxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% in oil; 0.42 g) was cautiously added to a solution of propanol (0.6 g) in DMF (8 ml). After gas evolution ceased, methyl 4-bromomethylbenzoate (1.0 g) was added. After 4 hours, the mixture was partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was hydrolyzed by method P-a. This resulted in the product with the molecular weight of 194.23 (C11H14O3); MS (ESI): 195 (M+H+).

Workup

  1. customthe mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThis resulted in the product with the molecular weight of 194.23 (C11H14O3)

Sources & evidence

ORD record
ord-4b7bbafada98422786be4672dd5d094c
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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