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

HRID 280402노트

반응식

HRID 280402 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 106560602,6-Dimethoxy-4-tert-butylphenol수율 89%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매2회

실험 절차

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%.

후처리

  1. customprepared

출처 및 근거

ORD 기록
ord-0a4fbec833074cdc93f4b29bab990c62
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588835

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