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

HRID 892154Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 60 °C

Procedure

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)+.

Workup

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

Sources & evidence

ORD record: ord-b9fa7fc851564ba8bade906282d5fb02
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005440B1

Reaction notes

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