Water → HCID 67450496, compound

HRID 595343Notes

Reaction equation

HRID 595343 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].[C:11]1([CH2:17][O:18][CH2:19][CH2:20][CH2:21]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O.C(OCC)(=O)C>[C:11]1([CH2:17][O:18][CH2:19][CH2:20][CH2:21][O:10][C:8]2[CH:9]=[C:4]([C:2](=[O:3])[CH3:1])[CH:5]=[CH:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 84873-HydroxyacetophenoneHCID 10796Cesium carbonateHCID 2776064Benzyl 3-Bromopropyl Ether

Product 1

HCID 67450496HCID 67450496, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-hydroxyacetophenone (5.5 g) in dimethylformamide (18 mL) was added 3-bromopropyl phenylmethyl ether (9.25 g) at ambient temperature followed by cesium carbonate (17 g). The suspension was stirred for 24 h and water was added followed by ethyl acetate. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The organic layers were combined and washed twice with 2 N sodium hydroxide, four times with brine, and concentrated in vacuo to an oil to give the title compound.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. washwashed twice with 2 N sodium hydroxide, four times with brine
  4. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-2e4b6da0190d48c0a91d1899ec7567ab
Source dataset
uspto-grants-2016_01
Patent number
US09243003B2

Reaction notes

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