Water → HCID 25056515, compound

Participants

Reaction Steps

To the suspension of Sodium Hydride (1.516 g, 95%, 60 mmol) in tetrahydrofuran (150 ml), 2-Methyl-prop-2-en-1-ol (4.323 g, 4.1 ml, 60 mmol) was added. After the reaction mixture was refluxed for 30 min, 3-Chloromethyl-benzoic acid (4.10 g, 24 mmol) was added and the reaction was kept to reflux for additional 10 h. After cooling down, water (100 ml) was added and the tetrahydrofuran was removed under vacuum. This resulting aqueous solution was adjusted with 6N HCl to pH 2 at 5° C., and the mixture was extracted with Et2O (50 ml×3). The organic phase was combined and washed with water (10 ml×2) respectively. The ether extract was dried with anhydrous sodium sulfate and then concentrated to give 3-(2-Methyl-allyloxymethyl)-benzoic acid as colorless oil (4.25 g, 85.9%). 1H-NMR (400 MHz, d6-DMSO): 7.90 (m, 1 arom.H); 7.85 (m, 1 arom.H); 7.55 (m, 1 arom.H); 7.45 (m, 1 arom.H); 4.96, 4.88 (2 s-like; C═CH2); 4.50 (s, —OCH2—C6H4); 3.90 (s, CH2O); 1.69 (s, CH3). 13C-NMR (100 MHz, d6-DMSO): 167.22 (—C═O); 142.03; 139.00; 131.72; 130.78; 128.56; 128.31; 128.07; 111.71; 73.41; 70.58; 19.30.

Provenance & Evidence