Quinizarin → 1,4-Anthraquinone

HRID 2306895

반응식

HRID 2306895 반응식
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

참가 물질

6

반응물 3

HCID 6688QuinizarinHCID 831071,4-DimethoxyanthraceneHCID 4311764Sodium borohydride2회

생성물 1

HCID 694571,4-Anthraquinone수율 95%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8150Diglyme용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2846e1f06cac499386558423024d60af
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828450B2

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