Sodium Hydroxide → 2,4-Bis-benzyloxy-5-tert-butyl-benzoic acid

HRID 41386ノート

反応式

HRID 41386 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:27](=[O:29])C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:30].[Na+].BrBr>O1CCOCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]([CH3:24])([CH3:26])[CH3:25])=[CH:11][C:10]=1[C:27]([OH:29])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 247734531-(2,4-Bis-benzyloxy-5-tert-butyl-phenyl)-ethanone

生成物 1

HCID 469156392,4-Bis-benzyloxy-5-tert-butyl-benzoic acid収率 79%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

1-(2,4-Bis-benzyloxy-5-tert-butyl-phenyl)-ethanone [prepared as per WO 2004/072051] (2.02 g, 5.2 mmol) was dissolved in 1,4-dioxane (30 ml), a solution of sodium hydroxide (2.08 g, 52.0 mmol) in water (30 ml) was added and the mixture was stirred and treated dropwise with bromine (0.8 ml, 15.6 mmol). The resulting mixture was stirred at room temperature for 16 hours. The 1,4-dioxane was removed in vacuo and the mixture acidified to pH 2 or below by the addition of 2M hydrochloric acid. The mixture was extracted with ethyl acetate, the organic layer was separated, the solvent removed in vacuo and the residue subjected to column chromatography on silica. Elution with 30% ethyl acetate in petroleum ether afforded 2,4-bis-benzyloxy-5-tert-butyl-benzoic acid (1.6 g, 79%) as a pale yellow oil. 1H NMR (DMSO-d6) 12.18 (1H, br s), 7.69 (1H, s), 7.52 (4H, t), 7.45-7.33 (6H, m), 6.93 (1H, s), 5.24 (2H, s), 5.23 (2H, s), 1.32 (9H, s). MS: [M+H]+ 391.

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 16 hours
  2. customThe 1,4-dioxane was removed in vacuo
  3. additionthe mixture acidified to pH 2 or below by the addition of 2M hydrochloric acid
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe organic layer was separated
  6. customthe solvent removed in vacuo
  7. washElution with 30% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-b8b38b34f9f7471c96a6178bf2f84b7e
出典データセット
uspto-grants-2013_09
特許番号
US08530469B2

反応ノート

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