반응 #41268

반응 방정식

CH3I

NaH

Methyl 6-(3-adamantyl-4-hydroxyphenyl)naphtoate

water

→

methyl 6-(3-adamantyl-4-methoxyphenyl)naphtoate

수율 57.2%

용매

DMF

반응 조건

후처리

1. 1
   온도cooled
2. 2
   workup.WAITleft 90 min at r.t
3. 3
   추출extraction with CH2Cl2
4. 4
   건조with EtOAc, drying
5. 5
   기타evaporating the joined organic phases, and chromatography (silicagel, hexane/EtOAc 9/1)

실험 절차

Methyl 6-(3-adamantyl-4-hydroxyphenyl)naphtoate (506 mg, 1.23 mmol) was added to an ice-cooled suspension of NaH (80 mg, 60%) in dry DMF, the mixture stirred 1 h at 0° C., then added with 245 mg (1.7 mmol) of CH3I, and left 90 min at r.t. Taking up with 80 ml of cold water, repeated extraction with CH2Cl2, then with EtOAc, drying and evaporating the joined organic phases, and chromatography (silicagel, hexane/EtOAc 9/1) gave 300 mg of methyl 6-(3-adamantyl-4-methoxyphenyl)naphtoate. This compound (235 mg) was suspended in a 1M solution of NaOH in MeOH and the mixture was refluxed 8 h. Evaporation, taking up with water, addition of HCl and filtration gave 227 mg of 6-(3-adamantyl-4-methoxyphenyl)naphtoic acid, mp >300° C.

출처