Water → p-(Pentyloxy)acetophenone

HRID 1408302Notes

Reaction equation

HRID 1408302 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O>CN(C=O)C>[CH2:18]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 74694'-HydroxyacetophenoneHCID 80571-BromopentaneHCID 11430Potassium Carbonate

Product 1

HCID 79598p-(Pentyloxy)acetophenoneYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the 4-hydroxyacetophenone (1.0 g, 7.3 mmol) in 5 mL DMF under Ar was added K2CO3 (1.0 g, 7.3 mmol) and 1-bromopentane (1.1 mL, 8.7 mmol) and heated at 60° C. overnight. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with EtOAc. The organic layer was washed with brine, dried and evaporated to afford a residue which upon purification by combiflash, eluting with 5% EtOAc in Hexane afforded 1.3 g product (86%). 1H NMR (500 MHz, CDCl3): δ 0.98 (t, 3H, J=7.0 Hz), 1.41-1.49 (m, 4H), 1.83-1.86 (m, 2H), 2.59 (s, 3H), 4.09 (t, 2H, J=6.5 Hz), 6.98 (d, 2H, J=7.0 Hz), 7.98 (d, 2H, J=7.0 Hz).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customdried
  5. customevaporated
  6. customto afford a residue which
  7. customupon purification by combiflash
  8. washeluting with 5% EtOAc in Hexane

Sources & evidence

ORD record
ord-bcf38dcb43ad411998ef5829a0eff581
Source dataset
uspto-grants-2014_12
Patent number
US08921309B2

Reaction notes

Loading…