Water → 2-(4-Isobutylphenyl)-2-hydroxypropionic Acid
Reaction equation
Cl[C:2](Cl)(C)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=1)=[O:4].[OH-:17].[Na+].[OH2:19].[C:20]1(C)C(C)=CC=CC=1>>[CH2:11]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([OH:4])([CH3:2])[C:20]([OH:19])=[O:17])=[CH:10][CH:9]=1)[CH:12]([CH3:13])[CH3:14]Participants
Conditions
- Temperature
- 20 °C
Procedure
Into a 500 ml-bomb-apparatus, were introduced 2 g (7.7×10-3 mol) of 2,2-dichloro-1-(4-isobutyl-phenyl)-1-propanone (G.P.C.: 95.4%), 7.2 g (0.18 mol) of sodium hydroxide in pellets, 200 ml of water and 40 ml of xylene. The mixture was brought to 200° C. and stirred for 1 hour at this temperature. The inner pressure in the bomb-apparatus was about 14 bars. After cooling at 20° C., the medium was decanted and the aqueous phases were re-extracted with ethyl ether. After acidification at pH=1 with concentrated hydrochloric acid, the medium was again extracted with ethyl ether. These last ethereal phases were washed with water, dried on sodium sulphate and brought to dryness under vacuum. In this manner, 1.60 g of 2-(4-isobutyl-phenyl)-2-hydroxy-propionic acid were obtained titrating 91.6% in G.P.C. namely a molar yield of 89.8%. An analytical sample was prepared by crystallisation from hexane.
Workup
- customwas brought to 200° C.
- customthe medium was decanted
- extractionthe aqueous phases were re-extracted with ethyl ether
- extractionAfter acidification at pH=1 with concentrated hydrochloric acid, the medium was again extracted with ethyl ether
- washThese last ethereal phases were washed with water
- customdried on sodium sulphate
Sources & evidence
- ORD record
- ord-53851eb285e74fab88ef69766f743935
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04713485
Reaction notes
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