Potassium Carbonate → tert-Butyl [4-(cyanomethyl)phenoxy]acetate

HRID 840432Notes

Reaction equation

HRID 840432 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:16]([O:15][C:13]([CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 15036608tert-Butyl [4-(cyanomethyl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3 g of p-hydroxyphenylacetonitrile, 3.6 ml of t-butyl bromoacetate, 6.5 g of potassium carbonate in 45 ml of dimethylformamide is stirred at room temperature for 16 hours. After dilution with water the product is extracted with ether. The ethyl layer is washed with 1N sodium hydroxide, dried over magnesium sulfate and the solvent removed in vacuo to yield p-(t-butoxycarbonylmethoxy)-phenylacetonitrile which is reduced to p-(t-butoxycarbonylmethoxy)-2-phenethylamine with sodium borohydride/cobalt chloride as described for the starting material under (g).

Workup

  1. extractionAfter dilution with water the product is extracted with ether
  2. washThe ethyl layer is washed with 1N sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e835b0c9d8bc4bc1890963e3fb510dd0
Source dataset
uspto-grants-2002_04
Patent number
US06368573B1

Reaction notes

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