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2-Methylbenzenesulfonic acid → HCID 66978185, 화합물

HRID 2108928
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HRID 2108928 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][OH:16])[C:12]([OH:17])=[C:11]([CH3:18])[C:10]=1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(C)[C:21](S(O)(=O)=O)=CC=C[CH:25]=1>COC(OC)(C)C>[CH2:1]([O:8][C:9]1[C:10]([CH3:19])=[C:11]([CH3:18])[C:12]2[O:17][C:20]([CH3:21])([CH3:25])[O:16][CH2:15][C:13]=2[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 69252-Methylbenzenesulfonic acidHCID 86597176HCID 86597176, 화합물

생성물 1

HCID 66978185HCID 66978185, 화합물수율 709%

시약·촉매·용매 1

HCID 64952,2-Dimethoxypropane용매

실험 절차

A solution of 4-benzyloxy-6-hydroxymethyl-2,3-dimethyl-phenol (86 mg, 0.33 mmol) in dimethoxypropane (10 mL) in the presence of toluene sulfonic acid (7 mg) was stirred at RT for 15 h. It was added 30 mg of anion-exchange resin and stirring was continued for 20 more min. The resin was then filtered off and the solution was concentrated. The crude product was purified on silicagel column chromatography to afford 6-benzyloxy-2,2,7,8-tetramethyl-4H-benzo[1,3]dioxine as a white sticky solid (86 mg). 1H-NMR (CDCl3, 300 MHz) δ (ppm): 7.51-7.35 (m, 5H), 6.45 (s, 1H), 5.02 (s, 2H), 4.85 (s, 2 H), 2.26 (s, 3H), 2.19 (s, 3H), 1.59 (s, 6H); 13C-NMR δ (ppm): 150.6, 143.3, 137.8, 128.5, 127.8, 126.3, 125.8, 115.9, 105.4, 99.1, 70.9, 61.1, 24.9, 12.2, 11.5.

후처리

  1. additionIt was added 30 mg of anion-exchange resin
  2. filtrationThe resin was then filtered off
  3. concentrationthe solution was concentrated
  4. customThe crude product was purified on silicagel column chromatography

출처 및 근거

ORD 기록
ord-22b721c967cb4df79f07a9ab2031419f
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07514461B2

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