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Benzoic Acid → Methyl 3,5-diallyloxy-2-benzoyl-6-ethylphenylacetate

HRID 499871
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HRID 499871 반응식
[CH2:1]([O:4][C:5]1[C:6]([CH2:20][CH3:21])=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3].[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[CH2:12]([O:11][C:9]1[C:8]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:6]([CH2:20][CH3:21])=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[CH:10]=1)[CH:13]=[CH2:14]
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참가 물질

6

반응물 4

HCID 243Benzoic AcidHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 23116370Methyl 3,5-diallyloxy-2-ethylphenylacetate

생성물 1

HCID 86610520Methyl 3,5-diallyloxy-2-benzoyl-6-ethylphenylacetate수율 56.6%

시약·촉매·용매 1

HCID 6422
Trifluoroacetic acid
용매

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온도
4 °C

실험 절차

Methyl 3,5-diallyloxy-2-ethylphenylacetate (0.31 g, 1.3 mmol) obtained in Example 5, Step 3 was dissolved in trifluoroacetic acid (2.0 mL). After the solution was cooled to 4° C., benzoic acid (0.40 g, 3.3 mmol) and trifluoroacetic anhydride (1.0 mL) were added thereto, followed by stirring for 18 hours, while the temperature of the reaction mixture was raised to room temperature. The reaction mixture was gradually added to a saturated aqueous solution of sodium hydrogencarbonate for neutralization, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/4) to obtain methyl 3,5-diallyloxy-2-benzoyl-6-ethylphenylacetate (0.29 g, 55%).

후처리

  1. temperaturewas raised to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/4)

출처 및 근거

ORD 기록
ord-f7f96e08ea664245863ca7d0725fc333
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07767693B2

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