1-Propanol → 4-(Propoxymethyl)benzoic acid

HRID 1354791Notes

Reaction equation

HRID 1354791 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-6de4782efa23483785ee29203c2ed656
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

Loading…