반응 #476236

반응 방정식

Et3N

oxalyl chloride

DMSO

citric acid

1-naphthalenemethanol

→

oil

수율 98.3%

1-Naphthalenecarboxaldehyde

수율 98.3%

용매

CH2Cl2

water

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for 10 min
2. 2
   workup.WAITAfter 3.5 h
3. 3
   세척The organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL)
4. 4
   건조dried (anhydrous MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   workup.ADDITIONEther-hexane (1:1) was added
8. 8
   여과the mixture was filtered
9. 9
   농축Concentration

실험 절차

To a cold (−78° C.) solution of oxalyl chloride (6.9 mL, 0.079 mol) in dry CH2Cl2 (200 mL) was added dropwise dry DMSO (11.2 mL, 0.158 mol). The mixture was stirred for 10 min, and then a solution of 1-naphthalenemethanol (10.0 g, 0.063 mot) in dry CH2Cl2 (40 mL) was added over 15 min. The mixture was stirred for 10 min, and then Et3N (44 mL, 0.316 mol) was added slowly. The reaction mixture was allowed to warm to room temperature. After 3.5 h, to the pale yellow heterogeneous mixture was added 10% aqueous citric acid (30 mL) and water (100 mL). The organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL), dried (anhydrous MgSO4), filtered, and concentrated. Ether-hexane (1:1) was added, and the mixture was filtered. Concentration provided a pale orange oil (9.7 g).

출처