Diethyl Ether → 3-Allyl-4-hydroxybenzonitrile

HRID 861429Notes

Reaction equation

HRID 861429 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9]CC=C)=[CH:5][CH:4]=1)#[N:2].C(OCC)C.[C:18]1(OC2C=CC=CC=2)[CH:23]=CC=C[CH:19]=1>>[CH2:23]([C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=1[OH:9])[CH:18]=[CH2:19]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7583Diphenyl EtherHCID 2579494-(ALLYLOXY)BENZONITRILE

Product 1

HCID 2584423-Allyl-4-hydroxybenzonitrile

Procedure

A solution of allyl 4-cyanophenyl ether (12 g) in diphenylether (20 ml) was heated at 260° C. for 30 minutes. The reaction mixture was cooled to ambient temperature, diethyl ether was added and the mixture was extracted with 1M aqueous sodium hydroxide solution. The aqueous phase was separated, acidified with 2M aqueous hydrochloric acid solution and extracted with diethyl ether. The organic phase was separated, dried (MgSO4) and evaporated to give 2-allyl-4-cyanophenol as a solid (11.4 g), m.p. 70° C.; microanalysis, found: C, 73.7; H, 5.6; N, 9.2%; C10H9NO. 0.25H2O requires: C, 73.4; H, 5.8; N, 8.6%; NMR: 3.2-3.5(2H,d), 5.0-5.1(2H,m), 5.85-6.05(1H,m), 6.9-7.0(1H,d), 7.4-7.5(2H,m) and 10.6(1H,s).

Workup

  1. extractionthe mixture was extracted with 1M aqueous sodium hydroxide solution
  2. customThe aqueous phase was separated
  3. extractionextracted with diethyl ether
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-5be61e901c624ed4a108547e93971aaa
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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