Quinizarin → 1,4-Anthraquinone

HRID 2306895

反応式

HRID 2306895 の反応式
C[O:2][C:3]1[C:16]2[C:7](=[CH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([O:17]C)=[CH:5][CH:4]=1.C1C=CC2C(=O)C3C(=C(O)C=CC=3O)C(=O)C=2C=1.[BH4-].[Na+]>COCCOCCOC.CO>[C:3]1(=[O:2])[C:16]2[C:7](=[CH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6](=[O:17])[CH:5]=[CH:4]1

参加物

6

反応物 3

HCID 6688QuinizarinHCID 831071,4-DimethoxyanthraceneHCID 4311764Sodium borohydride2 回

生成物 1

HCID 694571,4-Anthraquinone収率 95%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8150Diglyme溶媒

実験手順

Although the preparation of 1,4-dimethoxyanthracene (1) has been reported (Criswell, et al., J. Org. Chem. 1974, 39, 770-774) by using methylation of quinizarin (3) followed by sequential reduction of the diketo function with sodium borohydride in diglyme, the difficulty in the reduction steps prompted us to investigate an easier method in the preparation of 1. Reduction of 3 with sodium borohydride in MeOH followed by quenching with HCl gave a 95% yield of 1,4-anthraquinone (4) (Scheme 2). Reduction of the quinone moiety of 4 with aqueous sodium hydrosulfite in 1,4-dioxane provided 1,4-dihydroxyanthracene (5). Methylation of 5 with sodium hydride in DMF at room temperature gave excellent yield of 1.

後処理

  1. customin the preparation of 1
  2. customby quenching with HCl

出典と根拠

ORDレコード
ord-2846e1f06cac499386558423024d60af
出典データセット
uspto-grants-2004_12
特許番号
US06828450B2

関連ノート

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