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

반응식

[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]

참가 물질

반응물 4

HCID 6342Acetonitrile

HCID 7864Chloromethyl Methyl Ether2회

HCID 11430Potassium Carbonate2회

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

생성물 1

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

실험 절차

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.