Pyrogallol → 2,6-Dimethoxy-4-tert-butylphenol

HRID 280402ノート

反応式

HRID 280402 の反応式
[Na].[C:2]1(C=CC=C(O)C=1O)[OH:3].Br[C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:15]=[C:14](Br)[C:13]=1[OH:23].[CH3:24][O-:25].[Na+]>[Cu](I)I.CN(C)C=O>[CH3:2][O:3][C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:15]=[C:14]([O:25][CH3:24])[C:13]=1[OH:23]

参加物

7

反応物 4

HCID 1057PyrogallolHCID 2525182,6-Dibromo-4-tert-butylphenolHCID 5360545SodiumHCID 10942334Sodium Methoxide

生成物 1

HCID 106560602,6-Dimethoxy-4-tert-butylphenol収率 89%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

Processes are well known for preparing alkoxyphenols from phenol halides, in other words, for substituting alkoxyl groups for the halogen substituents in phenols. Usually alkoxyphenols are produced by reacting with heating a phenol halide with an alcoholate prepared by dissolving metallic sodium in an alcohol, in a suitable solvent, such as dimethylformamide or an amine, in the presence of a copper halide serving as a catalyst. Laid-Open West German Patent Application No. 2627874 and Chemical Abstract 86, 171074 (1974), for example, disclose a process for synthesizing pyrogallol in which 2,6-dibromo-4-tert-butylphenol is reacted with sodium methoxide with use of copper iodide as a catalyst and dimethylformamide as a solvent to afford 2,6-dimethoxy-4-tert-butylphenol in a yield of 89%. Journal of Chemical Society (C), 312 (1969) further discloses that several kinds of aromatic halides, including phenol bromide, are reacted with sodium methoxide in a mixture of methanol and collidine with use of copper iodide as a catlyst to give the corresponding methoxidated aromatic compounds in yields of 37 to 99%.

後処理

  1. customprepared

出典と根拠

ORDレコード
ord-0a4fbec833074cdc93f4b29bab990c62
出典データセット
uspto-grants-1986_05
特許番号
US04588835

反応ノート

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