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

HRID 5028
ノート
印刷プレビュー

反応式

HRID 5028 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒
HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-102bee15751b4b71bb53e4792a6e7427
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05242944

反応ノート

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