Water → HCID 23083071, compound

HRID 1678573Notes

Reaction equation

HRID 1678573 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[C:21]1([CH2:20][CH2:19][CH2:18][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 2736435Ethyl 4-hydroxyhydrocinnamate

Product 1

HCID 23083071HCID 23083071, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ice-cooled ethyl 4-hydroxybenzenepropanoate (0.40 g, 2.1 mmol) in N,N-dimethylformamide (15 mL) was added 60% sodium hydride (0.11 g, 2.7 mmol), and the mixture was stirred for 30 minutes. Then, 1-bromo-3-phenylpropane (0.53 g, 2.7 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water, dried, and then concentrated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.29 g, yield 46%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=18:1)

Sources & evidence

ORD record
ord-5e799f3a26964f4cb4d4bb6d52b57c86
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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