Hydrochloric Acid → 1-Hydroxy-3-phenylmethoxyxanthen-9-one

HRID 83098

반응식

HRID 83098 반응식
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>O.CC(C)=O>[CH2:24]([O:17][C:4]1[CH:3]=[C:2]([OH:1])[C:15]2[C:14](=[O:16])[C:13]3[C:8]([O:7][C:6]=2[CH:5]=1)=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 54881931,3-Dihydroxy-xanthone

생성물 1

HCID 57412951-Hydroxy-3-phenylmethoxyxanthen-9-one수율 42.6%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

The compound (1.77 g, 7.75 mmol) synthesized in Step 1 of Example 2 and K2CO3 (2.76 g, 0.02 mol) were charged to a dry round-bottom flask, and anhydrous acetone (200 mL) was added thereto. To the reaction mixture was added benzyl bromide (1.38 mL, 11.63 mmol), followed by stirring under reflux at 60° C. for one day. After the reaction was completed, the reaction liquid was cooled to room temperature, and 200 mL of water was added thereto. The reaction liquid was acidified with 3M-HCl and extracted twice with ethyl acetate. The organic layer was combined, successively washed with water and brine, and then dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: CH2Cl2) to give the title compound (1.05 g, 42.6%) as a light yellow solid.

후처리

  1. customthe reaction liquid
  2. temperaturewas cooled to room temperature
  3. customThe reaction liquid
  4. extractionextracted twice with ethyl acetate
  5. washsuccessively washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customThe resulting residue was separated
  9. custompurified by silica gel column chromatography (developing solvent: CH2Cl2)

출처 및 근거

ORD 기록
ord-f743684ac5604071bf5504ab69ea08ef
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846749B2

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