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

HRID 1073138Notes

Reaction equation

HRID 1073138 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-edc9444dbbe44b11a3a802c476e087a8
Source dataset
uspto-grants-1990_11
Patent number
US04968697

Reaction notes

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