METHYL 2-TRIFLUOROMETHANESULFONYLOXY-1-NAPHTHOATE synthesis
- Product Name:METHYL 2-TRIFLUOROMETHANESULFONYLOXY-1-NAPHTHOATE
- CAS Number:200573-11-1
- Molecular formula:C13H9F3O5S
- Molecular Weight:334.27
1634-04-4
651 suppliers
$14.00/100g
947-65-9
82 suppliers
$97.00/10g
200573-11-1
11 suppliers
$68.09/5g
Yield:-
Reaction Conditions:
with pyridine;trifluoromethanesulfonic acid anhydride in dichloromethane;toluene
Steps:
2 Preparation 2
Preparation 2 Methyl 2-trifluoromethanesulfonyloxy-1-naphthoate Trifluoromethanesulfonic anhydride (492 g, 1.74 mol, 1.1 eq) in dichloromethane (0.5 L) was added over 1.5 hours to a suspension of methyl 2-hydroxy-1-naphthoate (319 g, 1.58 mol) and pyridine (330 ml, 4.08 mol, 2.6 eq) in dichloromethane (1.7 L) maintained at an internal temperature between -70 and -50° C., under nitrogen. Once the addition was complete, the mixture was allowed to warm to ambient temperature and stirred for 16 hours, after which time all solids had dissolved. Methyl tert-butyl ether (MTBE, 2.5 L) was added, causing precipitation. The solids were removed by filtration and washed with MTBE (0.5 L). The MTBE solutions were combined and washed with 2 N HCl(aq) (0.3 L then 0.2 L), water (2*2.5 L) and brine (2 L). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was dissolved in toluene (2.5 L) and washed with 1 N NaOH (aq) (0.5 L), water (2.5 L) and brine (1 L). The toluene solution was dried (MgSO4), filtered and concentrated under reduced pressure. Initially a slightly brown oil, the product crystallized on standing. Yield 438.5 g, 83%
References:
Chirotech Technology, Ltd. US6320068, 2001, B1
358-23-6
575 suppliers
$10.00/1g
947-65-9
82 suppliers
$97.00/10g
200573-11-1
11 suppliers
$68.09/5g