Dimethyl Sulfate → Methyl 2-hydroxy-5-isopropyl-4-methoxybenzoate

反応式

[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:16])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

実験手順

A mixture of methyl 2,4-dihydroxy-5-isopropylbenzoate (420 mg, 2.0 mmol) and anhydrous potassium carbonate (331 mg, 2.4 mmol) in acetonitrile (10 ml) was treated with dimethyl sulphate (0.2 ml, 2.1 mmol) and the mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (10 ml). The solid material was collected by suction filtration, rinsed with water (2×10 ml) and sucked dry under reduced pressure to afford methyl 2-hydroxy-5-isopropyl-4-methoxybenzoate (440 mg, 98%) as a colourless solid. 1H NMR (DMSO-d6) 10.70 (1H, br s), 7.54 (1H, s), 6.53 (1H, s), 3.87 (3H, s), 3.84 (3H, s), 3.12 (1H, m), 1.13 (6H, d). MS: [M+H]+ 225.