Benzyl Chloride → Methyl 4-(benzyloxy)-3,5-dimethoxybenzoate

Benzyl chloride (11.04 g, 86.9 mmol) was added to a stirred solution of 121 (19.22 g, 90.8 mmol) over K2CO3 (6.59 g, 47.7 mmol) in anhydrous MeOH (175 mL) and the mixture was heated at reflux for 12 h. Excess solvent was removed under reduced pressure and the residue was extracted with benzene (3×100 mL). The organic layer was washed with H2O (3×100 mL), brine (3×100 mL) and dried over anhydrous MgSO4. Evaporation of the solvent afforded an orange oil which crystallised on standing. The solid was redissolved in EtOAc, and briefly washed with 1N NaOH (100 mL), H2O (100 mL), brine (100 mL) and dried over MgSO4. Evaporation of excess solvent yielded the product as a yellow solid 122 (19.20 g, 63.6 mmol); 1H NMR (270 MHz, CDCl3) δ3.8 (s, 3H), 3.85 (s, 3H), 3.9 (s, 3H), 5.1 (s, 2H), 7.3-7.5 (m, 7H); 13C NMR (67.8 MHz, CDCl3) δ166.7, 153.2, 140.8, 137.3, 128.7, 128.6, 128.4, 128.4, 128.2, 128.0, 127.7, 125.3, 106.7, 74.9, 56.1, 52.2.

1. temperaturethe mixture was heated
2. temperatureat reflux for 12 h
3. customExcess solvent was removed under reduced pressure
4. extractionthe residue was extracted with benzene (3×100 mL)
5. washThe organic layer was washed with H2O (3×100 mL), brine (3×100 mL)
6. dry with materialdried over anhydrous MgSO4
7. customEvaporation of the solvent
8. customafforded an orange oil which
9. customcrystallised
10. dissolutionThe solid was redissolved in EtOAc
11. washbriefly washed with 1N NaOH (100 mL), H2O (100 mL), brine (100 mL)
12. dry with materialdried over MgSO4
13. customEvaporation of excess solvent

ORD record

ord-cacb73829cc64e859dee84058f2149fd

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067511B2