Resorcinol → (2-[3-Hydroxyphenoxymethyl]-6-methylphenoxy)acetonitrile

HRID 892154ノート

反応式

HRID 892154 の反応式
[C:1]([CH2:3][O:4][C:5]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Br)#[N:2].[C:14]1([CH:21]=[CH:20][CH:19]=[C:17]([OH:18])[CH:16]=1)[OH:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCOCC>[OH:15][C:14]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[O:18][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:12]([CH3:13])[C:5]=1[O:4][CH2:3][C:1]#[N:2]

参加物

6

反応物 3

HCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 222414892-Cyanomethoxy-3-methylbenzyl bromide

生成物 1

HCID 22241289(2-[3-Hydroxyphenoxymethyl]-6-methylphenoxy)acetonitrile

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

Heated (60° C.) a mixture of 2-cyanomethoxy-3-methylbenzyl bromide (10.2 g, 42.7 mmoles, example 24), resorcinol (18.8 g, 171 mmoles), and potassium carbonate (47.2 g, 342 mmoles) in acetonitrile (140 mL) for two hours. The reaction is diluted with ether and washed three times with distilled water, once with brine, and dried over MgSO4. The organic layer is isolated and concentrated, and the resulting residue is purified by column chromatography (silica, 5% EtOAc/CH2Cl2) to yield the title compound as a white crystalline solid. MS(EI) 269 (M)+.

後処理

  1. washwashed three times with distilled water
  2. dry with materialonce with brine, and dried over MgSO4
  3. customThe organic layer is isolated
  4. concentrationconcentrated
  5. customthe resulting residue is purified by column chromatography (silica, 5% EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-b9fa7fc851564ba8bade906282d5fb02
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

読み込み中…