Hydrochloric Acid → 2,4-Bis(benzyloxy)-5-isopropenylbenzoic acid

HRID 41390

反応式

HRID 41390 の反応式
C([O:8][C:9](=[O:35])[C:10]1[CH:15]=[C:14]([C:16]([CH3:18])=[CH2:17])[C:13]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:12][C:11]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)C1C=CC=CC=1.[OH-].[Li+].Cl>C1COCC1.CO.O.O>[CH2:28]([O:27][C:11]1[CH:12]=[C:13]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:14]([C:16]([CH3:18])=[CH2:17])=[CH:15][C:10]=1[C:9]([OH:35])=[O:8])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 592631182,4-Bis-benzyloxy-5-isopropenyl-benzoic acid benzyl ester

生成物 1

HCID 498640162,4-Bis(benzyloxy)-5-isopropenylbenzoic acid収率 81.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid benzyl ester (40.8 g, 87.9 mmol) in THF-MeOH-water (3:1:1, 300 mL total) was added lithium hydroxide (8.42 g, 352 mmol). The mixture was heated at 50° C. for 16 h, allowed to cool to ambient and then diluted with water (300 mL). The mixture was taken to pH˜1 using conc. HCl (−30 mL) and then extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and reduced in vacuo. The solid residue was taken up in P.E-MeOH (9:1, 300 mL total), the slurry stirred for 1 h at ambient and the solid collected by filtration. The solid was dried in vacuo to give the title compound (26.8 g) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) 12.30 (s, 1H), 7.61 (s, 1H), 7.53 (d, J=7.0 Hz, 2H), 7.47-7.31 (m, 8H), 6.94 (s, 1H), 5.23 (d, J=14.0 Hz, 4H), 5.08 (d, J=9.0 Hz, 2H), 2.04 (s, 3H).

後処理

  1. temperatureto cool to ambient and
  2. extractionextracted with EtOAc (2×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. filtrationcollected by filtration
  7. customThe solid was dried in vacuo

出典と根拠

ORDレコード
ord-1b2133e667754c7fa1d1e0eb664f0358
出典データセット
uspto-grants-2013_09
特許番号
US08530469B2

関連ノート

読み込み中…