Sodium Hydroxide → 2-(p-Toluenesulfonyloxy)acetic Acid

HRID 2422920ノート

反応式

HRID 2422920 の反応式
[S:1]([O:11][CH2:12][C:13]([O:15]CC)=[O:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH-].[Na+]>C(O)C>[S:1]([O:11][CH2:12][C:13]([OH:15])=[O:14])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 11821264Ethyl 2-(p-Toluenesulfonyloxy)acetate

生成物 1

HCID 2262662-(p-Toluenesulfonyloxy)acetic Acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of ethyl 2-(tosyloxy)acetate (2, 860 mg, 3.33 mmol) in ethanol (4 ml) was treated at room temperature with 5% NaOH aqueous solution (2 ml). The resulting mixture was stirred at room temperature for 3 h. The ethanol was removed in vacuo and aqueous 5% HCl solution (2.7 ml) was added. The aqueous mixture was extracted with chloroform and the organic extracts dried (Na2SO4), filtered and the solvent removed under reduced pressure. The remaining white solid was recrystallized from hexane/ethyl acetate as a white powder (476 mg, 62%). [This reaction was repeated on 2× scale (1.449 g, 94%)]. δH (400 MHz, MeOD) 2.45 (3H, s, Me), 4.58 (2H, s, CH2), 7.44 (2H, d, J=8.2 Hz, ArH), 7.82 (2H, d, J=8.2 Hz, ArH); δc (100.6 MHz, MeOD) 20.4, 64.7, 128.0, 129.9, 133.0, 145.6, 168.2; MS (ES+) 247.8 (100%, [M+H2O]+); MS (ES−) 170.1 (100%, TsO−).

後処理

  1. customThe ethanol was removed in vacuo and aqueous 5% HCl solution (2.7 ml)
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with chloroform
  4. dry with materialthe organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe remaining white solid was recrystallized from hexane/ethyl acetate as a white powder (476 mg, 62%)

出典と根拠

ORDレコード
ord-a0dc166af4a84344839a951390973bd9
出典データセット
uspto-grants-2011_06
特許番号
US07960434B2

反応ノート

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