3-Hydroxybenzyl alcohol → [2-(3-Hydroxymethyl-phenoxymethyl)-6-methyl-phenoxy]-acetonitrile

HRID 892198Notes

Reaction equation

HRID 892198 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].C([O-])([O-])=O.[K+].[K+].Br[CH2:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:19]=1[O:20][CH2:21][C:22]#[N:23]>CN(C=O)C.CCOCC>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:19]=1[O:20][CH2:21][C:22]#[N:23]

Participants

6

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 11430Potassium CarbonateHCID 222414892-Cyanomethoxy-3-methylbenzyl bromide

Product 1

HCID 22241439[2-(3-Hydroxymethyl-phenoxymethyl)-6-methyl-phenoxy]-acetonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxybenzyl alcohol (202 mg, 1.63 mmol) in DMF (5.4 mL) is added K2CO3 (247 mg, 1.79 mmol) and (2-bromomethyl-6-methyl-phenoxy)-acetonitrile (430 mg, 1.79 mmol, example 24). Heated resulting mixture to 60° C. and stirred for 3 hrs then cooled to room temp and diluted with ether. Washed organic layer with water, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 30% ethyl acetate in hexanes) to give the title compound. MS (EI) 283 (M)+.

Workup

  1. temperatureHeated
  2. customresulting mixture to 60° C.
  3. dry with materialWashed organic layer with water, brine, dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (silica, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7dc8e622e71e470095af48ed9ba9d451
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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