Chloroacetic Acid → Benzoic acid, 2-(carboxymethoxy)-

HRID 1362364

반응식

HRID 1362364 반응식
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[Na+].Cl[CH2:14][C:15]([OH:17])=[O:16]>O>[C:15]([CH2:14][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])([OH:17])=[O:16]

참가 물질

5

반응물 3

HCID 300Chloroacetic AcidHCID 338Salicylic AcidHCID 14798Sodium Hydroxide

생성물 1

HCID 69461Benzoic acid, 2-(carboxymethoxy)-수율 24%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of salicylic acid (20 g, 145 mmol) in water (200 mL) is added carefully sodium hydroxide (60 g, 1.45 mol) followed by chloroacetic acid (27 g, 290 mmol). The mixture is refluxed for 5 d, cooled to room temperature and the precipitate is filtered and dried. Trituration with hexanes yielded the title compound (6.84 g, 24%) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ 7.65-7.66 (dd, 1H, J=8.0, 2.0 Hz), 7.45-7.47 (dd, 1H, J=8.0, 2.0 Hz), 6.97-7.05 (m, 2H), 4.77 (s, 2H).

후처리

  1. temperatureThe mixture is refluxed for 5 d
  2. filtrationthe precipitate is filtered
  3. customdried

출처 및 근거

ORD 기록
ord-cb4210f1881b46afa449d7d980a42260
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

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