p-Toluenesulfonic acid → Methyl 4-bromo-alpha-hydroxybenzeneacetate

HRID 718642

반응식

HRID 718642 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13]OC(OC)(C)C.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 97930p-Bromomandelic acid

생성물 1

HCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
55 °C

실험 절차

To a solution of 2-(4-bromophenyl)-2-hydroxyacetic acid (5.0 g, 22 mmol) in MeOH (10 mL) was added 2,2-dimethoxypropane (3.4 g, 33 mmol) and 4-methylbenzene-1-sulfonic acid (2.0 mg, 0.010 mmol). The resulting solution was stirred overnight at 55° C. and allowed to cool to rt. The resulting mixture was concentrated under reduced pressure and poured into water (100 mL). The solids were collected by filtration and washed with hexanes (2×20 mL) to obtain compound 50a as a gray solid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.54-7.51 (m, 2H), 7.35-7.28 (m, 2H), 5.18-5.16 (m, 1H), 3.793 (s, 3H), 3.51-3.49 (m, 1H).

후처리

  1. temperatureto cool to rt
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionpoured into water (100 mL)
  4. filtrationThe solids were collected by filtration
  5. washwashed with hexanes (2×20 mL)

출처 및 근거

ORD 기록
ord-f3e6ec73f897426aa199a0c9f89ac2fe
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193736B2

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