Acetonitrile → Methyl 2,4-bis-(methoxymethyloxy)-5-isopropylbenzoate

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:19])([O-])[O-].[K+].[K+].[CH3:22][O:23][CH2:24]Cl.[C:26](#N)C>>[CH3:22][O:23][CH2:24][O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:26][O:19][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

反応物 4

HCID 6342Acetonitrile

HCID 7864Chloromethyl Methyl Ether2 回

HCID 11430Potassium Carbonate2 回

HCID 59167875Methyl 2,4-dihydroxy-5-isopropylbenzoate

生成物 1

HCID 58236468Methyl 2,4-bis-(methoxymethyloxy)-5-isopropylbenzoate収率 97%

実験手順

A mixture of methyl 2,4-dihydroxy-5-isopropylbenzoate (420 mg, 2.0 mmol) and anhydrous potassium carbonate (332 mg, 2.4 mmol) in acetonitrile (12 ml) was treated with chloromethyl methyl ether (0.16 ml, 2.1 mmol) and the mixture was stirred at room temperature for 16 hours whereupon further anhydrous potassium carbonate (1.38 g, 10.0 mmol) and chloromethyl methyl ether (0.76 ml, 10.0 mmol) were added and the mixture was stirred and held at 50° C. for a further 4 days. Upon cooling to room temperature the solvent was removed in vacuo and the residue treated with water (30 ml). The organic material was extracted with dichloromethane (2×20 ml) and the combined organic extracts were evaporated in vacuo to afford methyl 2,4-bis-(methoxymethyloxy)-5-isopropylbenzoate (580 mg, 97%) as a pale yellow oil. 1H NMR (DMSO-d6) 7.57 (1H, s), 6.88 (1H, s), 5.32 (2H, s), 5.20 (2H, s), 3.78 (3H, s), 3.41 (6H, s), 3.21 (1H, m), 1.17 (6H, d). MS: [M+Na]+ 321.