Nitric Acid → 2-(3-Methoxy-propyl)-4-nitro-phenoxy-acetic acid ethyl ester

HRID 1242279ノート

反応式

HRID 1242279 の反応式
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:19]([O-:21])=[O:20])=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH3:2]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 67072081HCID 67072081、化合物

生成物 1

HCID 670724332-(3-Methoxy-propyl)-4-nitro-phenoxy-acetic acid ethyl ester

試薬・触媒・溶媒 1

HCID 9845Trifluoroacetic anhydride溶媒2 回

実験手順

4.00 g (15.9 mmol) of the above prepared [2-(3-methoxy-propyl)-phenoxy]-acetic acid ethyl ester was dissolved in 5.0 ml of TFAA and added slowly and carefully via dropping funnel to a mixture of 5 ml of TFAA and 4 ml of conc. HNO3 (65%) kept at −10° C.; the reaction was then allowed to proceed for additional 30 Min. Careful quenching with ice, twofold extraction with AcOEt, washing with NaHCO3 and brine, drying over magnesium sulfate, and evaporation of the solvents left a crude product which was purified by flash chromatography (SiO2, hexane/AcOEt=75/25) to deliver finally 3.00 g of the title compound as light brown oil, contaminated according to NMR with roughly 35% of the ortho-isomer which was separated after the next step.

後処理

  1. additionadded slowly
  2. customkept at −10° C.
  3. customCareful quenching with ice, twofold extraction with AcOEt
  4. washwashing with NaHCO3 and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  6. waitleft a crude product which
  7. customwas purified by flash chromatography (SiO2, hexane/AcOEt=75/25)
  8. customwas separated after the next step

出典と根拠

ORDレコード
ord-7bb0b098c2b94abcb419ecdc53522f71
出典データセット
uspto-grants-2006_10
特許番号
US07115611B2

反応ノート

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