Acetone → Isopropyl 2-(3-isopropoxyphenyl)acetate

反応式

[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH:12](I)([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[CH3:22][C:23]([CH3:25])=O>>[CH:12]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH:23]([CH3:25])[CH3:22])[CH:3]=1)([CH3:14])[CH3:13]

参加物

反応物 4

HCID 180Acetone

HCID 6362Isopropyl iodide

HCID 11430Potassium Carbonate

HCID 121223'-Hydroxyphenylacetic acid

生成物 1

HCID 54166898Isopropyl 2-(3-isopropoxyphenyl)acetate

実験手順

Combine 3-hydroxy-phenyl acetic acid (9.26 g, 60.9 mmol), isopropyl iodide (42.6 g, 250 mmol), and acetone (80 mL). Add portionwise, potassium carbonate (16.9 g, 122 mmol). Heat to reflux with vigorous mechanical stirring. After 20 hours, cool to ambient temperature and evaporate in vacuo to give a residue. Partition the residue between diethyl ether and 5% sodium hydroxide solution. Extract the organic layer with water and a saturated sodium chloride solution. Dry the organic layer over MgSO4, filter and evaporate in vacuo to obtain a liquid. Bulb-to-bulb distillation gives 3-isopropoxy-phenyl-acetic acid isopropyl ester: bp; 125° C. at 0.2 mm of Hg.