Benzyl Bromide → 4-Benzyloxy-2-ethyl-3-methylbenzoic acid

反応式

[CH2:1]([C:3]1[C:11]([CH3:12])=[C:10]([OH:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH3:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:14]([O:13][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[C:3]([CH2:1][CH3:2])[C:11]=1[CH3:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

実験手順

2.10 g of 2-ethyl-4-hydroxy-3-methylbenzoic acid (E1) are dissolved in 50 ml of acetone. 3.30 ml of benzyl bromide and 5.10 g of K2CO3 are subsequently added. The reaction suspension is heated under reflux for 18 h overnight, subsequently filtered off with suction, and the filtrate obtained is evaporated to dryness in vacuo. The residue is dissolved in 40 ml of ethanol, and 40 ml of 2.0 N NaOH solution are added. The mixture is then heated under reflux for 3 h. The clear solution is diluted with 150 ml of water and adjusted to pH 1 using 20% hydrochloric acid. After stirring for 30 min, the precipitate formed is filtered off with suction, rinsed with water and dried at 90° C. in vacuo overnight, giving 2.45 g of the title compound as a beige, amorphous solid having a melting point of 169° C.; MS: 270.0 (M+); TLC: Rf=0.36 (cyclohexane/ethyl acetate 2:1 parts by volume).