2-Bromopropane → HCID 28562462, compound

HRID 2167119Notes

Reaction equation

HRID 2167119 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:11][OH:12].Br[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[CH:19]([O:7][C:8]1[CH:9]=[C:10]([CH2:11][OH:12])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 780893-Hydroxy-4-methoxybenzyl alcohol

Product 1

HCID 28562462HCID 28562462, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (13.5 g) was added to a solution of 3-hydroxy-4-methoxybenzyl alcohol (10.0 g) and 2-bromopropane (9.15 ml) in dry DMF (100 ml) and the mixture was heated to reflux for 72 hours. The solvent was removed under vacuum. The residue obtained was partitioned between water and ethyl acetate. The aqueous phase was re-extracted with ethyl acetate (2×) and the combined organics were passed through a hydrophobic frit. The solvents were removed under vacuum.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 72 hours
  3. customThe solvent was removed under vacuum
  4. customThe residue obtained
  5. customwas partitioned between water and ethyl acetate
  6. extractionThe aqueous phase was re-extracted with ethyl acetate (2×)
  7. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-3257c413fba34921963a686fd25ece58
Source dataset
uspto-grants-2015_06
Patent number
US09044463B2

Reaction notes

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