Trifluoroacetic acid → 4-(1-Ethoxyethoxy)-3-methoxybenzonitrile

HRID 325938Notes

Reaction equation

HRID 325938 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[OH:18])[C:13]#[N:14].[CH:19]([O:21][CH2:22][CH3:23])=[CH2:20].O1CCCC1>C(N(CC)CC)C>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH:19]([O:21][CH2:22][CH3:23])[CH3:20])[C:13]#[N:14]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8023Ethyl vinyl etherHCID 8028TetrahydrofuranHCID 781354-Hydroxy-3-methoxybenzonitrile

Product 1

HCID 132924914-(1-Ethoxyethoxy)-3-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Two ml trifluoroacetic acid was added slowly to a chilled solution of 20 g of 3-methoxy-4-hydroxybenzonitrile, 50.7 ml of ethyl vinyl ether and 50 ml tetrahydrofuran (THF). The mixture was stirred at room temperature overnight. 7.5 ml of triethylamine was added to the mixture and stirring was continued for several minutes followed by solvent evaporation. The residue was partitioned between 400 ml of ether and 100 ml 1 N NaOH. The remaining ether layer was washed with 100 ml H2O and with 100 ml brine, dried (MgSO4) and evaporated to yield 31.2 gm of crude 3-methoxy-4-(2-ethoxy-1-oxapropyl)benzonitrile.

Workup

  1. stirringstirring
  2. waitwas continued for several minutes
  3. customfollowed by solvent evaporation
  4. customThe residue was partitioned between 400 ml of ether and 100 ml 1 N NaOH
  5. washThe remaining ether layer was washed with 100 ml H2O and with 100 ml brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-7e3802a772014973a5471244814d9e93
Source dataset
uspto-grants-1984_04
Patent number
US04443473

Reaction notes

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