2'-Hydroxyacetophenone → (2-Acetylphenoxy)butanoic acid, ethyl ester

HRID 964448Notes

Reaction equation

HRID 964448 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])(=[O:3])[CH3:2].Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>[I-].[Na+]>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH:14]([CH2:13][CH3:12])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 83752'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 15741884(2-Acetylphenoxy)butanoic acid, ethyl esterYield 100.2%

Reagents, catalysts & solvents 1

HCID 5238Sodium IodideCatalyst

Procedure

2-Acetylphenol (1 g, 7.34 mmol) is treated with 1.79 g (9.18 mmol) of ethyl 4-bromobutyrate, 3.55 g (25.71 mmol) of potassium carbonate and a catalytic amount (11 mg, 0.07 mmol) of sodium iodide as described in Preparation 3 to give 1.84 g of (2-acetylphenoxy)butyric acid, ethyl ester as a light yellow oil which solidified upon standing: m.p. 43°-45° C.; The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 1730, 1660, 1600 cm-1 ; MS (CI) m/e 251 (M+H), 232, 205.

Sources & evidence

ORD record
ord-ecb49b9450dd46908e9df9b825a5455d
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Reaction notes

Loading…