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

HRID 892154노트

반응식

HRID 892154 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

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온도
60 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b9fa7fc851564ba8bade906282d5fb02
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

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