Acetonitrile → Methyl 2,4-bis-(methoxymethyloxy)-5-isopropylbenzoate
Reaction equation
[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]Participants
Procedure
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.
Workup
- additionwere added
- customwas removed in vacuo
- additionthe residue treated with water (30 ml)
- extractionThe organic material was extracted with dichloromethane (2×20 ml)
- customthe combined organic extracts were evaporated in vacuo
Sources & evidence
- ORD record
- ord-bb61448ba29a4ef0a019cc3c2a1c9563
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383619B2
Reaction notes
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