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

HRID 1462456Notes

Reaction equation

HRID 1462456 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

2 ml of 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 until the solvent was evaporated. The residue was partitioned between 400 ml of diethyl ether and 100 ml 1N NaOH. The diethyl ether layer was washed successively with 100 ml H2O and 100 ml brine, dried over MgSO4 and evaporated to yield 31.2 gm of 3-methoxy-4-(2-ethoxy-1-oxapropyl)benzonitrile.

Workup

  1. stirringstirring
  2. waitwas continued for several minutes until the solvent
  3. customwas evaporated
  4. customThe residue was partitioned between 400 ml of diethyl ether and 100 ml 1N NaOH
  5. washThe diethyl ether layer was washed successively with 100 ml H2O and 100 ml brine
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-1bd791cd891943d4bc9126c4b74ffaf4
Source dataset
uspto-grants-1984_07
Patent number
US04460602

Reaction notes

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