Sodium Iodide → 4-[4-(2-Hydroxyethoxy)phenyl]butan-2-one

HRID 851183Notes

Reaction equation

HRID 851183 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][OH:16].[OH-].[Na+].[I-].[Na+]>O>[OH:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 108982-BromoethanolHCID 14798Sodium HydroxideHCID 216484-(4'-Hydroxyphenyl)-2-butanone

Product 1

HCID 130796444-[4-(2-Hydroxyethoxy)phenyl]butan-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[4-hydroxyphenyl]butan-2-one (16.4 g], 2-bromoethanol (16.9 g), sodium hydroxide (7.5 g), sodium iodide (7.5 g) and water (200 ml) was heated under reflux for 4 hours, cooled and extracted with dichloromethane. The extract was washed with brine, dried (MgSO4) and evaporated to dryness. The residual oil was distilled to give the title compound as a colourless liquid, bp 170°-1°/0.8 mm. P τ(CDCl3) 7.85 (3H, s), 7.15-7.35 (4H, complex), 7.4-7.6 (1H, t), 5.85-6.25 (4H, complex), 2.8-3.4 (4H, dd).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. extractionextracted with dichloromethane
  5. washThe extract was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-802e2da9209748e99c0483369113dc5c
Source dataset
uspto-grants-1983_05
Patent number
US04382958

Reaction notes

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