Water → HCID 23083071, compound

HRID 2422199Notes

Reaction equation

HRID 2422199 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 an ice-cooled solution of 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 min. 1-Bromo-3-phenylpropane (0.53 g, 2.7 mmol) was added, and the mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.29 g, yield 46%). oil.

Workup

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

Sources & evidence

ORD record
ord-cbcd9af7a23442d0a788c4e533f210a4
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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