HCID 86662537, 화합물 → 2,3-Bis(4-methoxybenzyloxy)benzoic acid

HRID 75070

반응식

HRID 75070 반응식
COC1C=CC(C[C:8]2[CH:16]=[CH:15][C:11]([C:12]([O-:14])=[O:13])=[C:10]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:9]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=CC=1>O1CCOCC1.[OH-].[Na+]>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:10]2[C:9]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)=[CH:8][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[CH:24][CH:23]=1

참가 물질

4

반응물 1

HCID 86662537HCID 86662537, 화합물

생성물 1

HCID 216602332,3-Bis(4-methoxybenzyloxy)benzoic acid

시약·촉매·용매 2

HCID 14798Sodium Hydroxide용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 19 (8.60 g, 16.71 mmol) in dioxane (84 mL) and 2N NaOH (42 mL) was stirred for 24 h at room temperature. The reaction mixture was concentrated in vacuo. The residue was stirred with H2O (100 mL) and then acidified to pH 2 with 1N HCl. The white solid was filtered, washed with hexane, and was recrystallised from EtOAc/hexanes to generate 5.93 g (90%) of 20 as a white crystalline solid, mp 129° C.: 1H NMR δ 3.8 (s, 3H), 3.85 (s, 3H), 5.12 (s, 2H), 5.20 (s, 2H), 6.83 (d, 2H, J=8.8), 6.96 (d, 2H, J=9.2), 7.18 (t, 2H, J=8.0), 7.22-7.27 (m, 2H), 7.41 (d, 2H, J=8.4), 7.73 (dd, 1H, J=1.2, 8.0); 13C NMR δ 55.36, 55.37, 55.44, 55.46, 71.42, 114.26, 119.12, 123.04, 124.37, 125.00, 126.87, 128.02, 129.73, 131.21, 147.17, 151.45, 159.94, 160.44, 165.45; HRMS m/z calcd for C23H22NaO6, 417.1332 (M+Na); found, 417.1332.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe white solid was filtered
  3. washwashed with hexane
  4. customwas recrystallised from EtOAc/hexanes

출처 및 근거

ORD 기록
ord-1793864655f14db590a6fce23bdae282
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08834890B2

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