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Hydrochloric Acid → Ethyl [3-(benzyloxy)-4-hydroxyphenyl]acetate

HRID 5028
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HRID 5028 반응식
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([OH:13])[CH:7]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>CC(C)=O.O>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=1)[CH3:2]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15132249Ethyl 2-(3,4-dihydroxyphenyl)acetate

생성물 1

HCID 54479398Ethyl [3-(benzyloxy)-4-hydroxyphenyl]acetate수율 45%

시약·촉매·용매 2

HCID 180Acetone
용매
HCID 962Water용매

실험 절차

To a solution of 5.79 g of 3,4-dihydroxylphenyl acetic acid ethyl ester dissolved in dry acetone were added 4.48 g of potassium carbonate and 4.15 ml of benzyl bromide. The mixture was heated to reflux until the starting materials were exhausted; and then the solvent was distilled off under reduced pressure. To the residues thus obtained was added 50 ml of water; and the mixture was acidified with concentrated hydrochloric acid and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to obtain residues, which were purified by chromatography to provide 3.80 g (yield 45%) of 3-benzyloxy-4-hydroxyphenylacetic acid ethyl ester, having the characteristics of: NMR(CDCl3, 200 MHz) δ1.24(t, J=7 Hz, 3H, CH3), 3.45(s, 2H, CH2CO), 4.12(q, J=7 Hz, 2H, OCH2), 5.05(s, 2H, CH2Ph), 6.77-7.35(m, 6H, ArH).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux until the starting materials
  3. distillationand then the solvent was distilled off under reduced pressure
  4. customTo the residues thus obtained
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto obtain residues, which
  9. customwere purified by chromatography

출처 및 근거

ORD 기록
ord-102bee15751b4b71bb53e4792a6e7427
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05242944

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