4'-Hydroxyacetophenone → 1-[4-(Benzyloxy)phenyl]ethan-1-one

HRID 1383562Notes

Reaction equation

HRID 1383562 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1>[CH2:11]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4′-Hydroxyacetophenone (13.62 g, 100 mmol), benzylbromide (17.1 g, 100 mmol), and cesium carbonate (35.83 g, 100 mmol) were added to tetrahydrofuran at room temperature and stirred overnight. The product was concentrated to dryness and recrystallized from ether and hexane to yield 15 g of 4′-benzyloxyacetophenone which appeared as a white powder. An Rf of 0.42 was observed when resolved by thin layer chromatography using methylene chloride. 1H nmr (δ, ppm, CDCl3), 7.94 (2H, δ, 8.8 Hz, O—Ar—C(O)), 7.42 (5H, m, Ar′CH2O—), 7.01 (2H, δ, 8.8 Hz, O—Ar—C(O)), 5.14 (2H, s, Ar′CH2O—), 2.56 (3H, S, CH3).

Workup

  1. concentrationThe product was concentrated to dryness
  2. customrecrystallized from ether and hexane

Sources & evidence

ORD record
ord-29d64b67562446b7a9a55852bcf0615e
Source dataset
uspto-grants-2001_07
Patent number
US06255336B1

Reaction notes

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