반응 #1889312

반응 방정식

6-(benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol

p-toluenesulfonic acid monohydrate

toluene

→

product

수율 57.0%

7-(Benzyloxy)-3-bromo-1,2-dihydronaphthalene

수율 57.0%

용매

EtOAc hexane

반응 조건

후처리

1. 1
   세척washed with saturated NaHCO3, water, brine
2. 2
   건조dried over anhydrous Na2SO4
3. 3
   여과filtered
4. 4
   기타evaporated in rotavapor
5. 5
   기타to give a crude oil

실험 절차

The intermediate, 6-(benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol, was heated to reflux with p-toluenesulfonic acid monohydrate (0.916 g, 0.00482 mol) in toluene (300 mL, 3 mol) with a Dean-Stark tube for 1 hour, cooled to r.t., washed with saturated NaHCO3, water, brine, dried over anhydrous Na2SO4, filtered, evaporated in rotavapor to give a crude oil. Chromatograph with EtOAc:hexane (0:100 to 10:90) gave a solid product (17.29g, 57%). 1H NMR (CHLOROFORM-d) δ: 7.30-7.49 (m, 5H), 6.85-6.96 (m, 1H), 6.76 (m, 3H), 5.06 (s, 2H), 2.87-3.00 (m, 2H), 2.67-2.83 (m, 2H). MS (M+1): 316.0.

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