tert-Butanol → Tert-butyl 4-cyanobenzoate

HRID 979774Notes

Reaction equation

HRID 979774 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:12](O)([CH3:15])([CH3:14])[CH3:13].Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 120874-Cyanobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 271408Tert-butyl 4-cyanobenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Dissolve 22.1 g 4-cyanobenzoic acid and 28.2 ml t-butanol in 500 ml DMF. Add 9.15 g 4-(dimethylamino) pyridine and 31.5 g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. Stir the mixture overnight at RT. Remove the DMF in vacuo, and partition the resultant residue between ethyl acetate and water. Wash the organic layer successively with cold 0.5 N aqueous HCl, water, 5% aqueous NaHC03 and brine. Dry the organic layer over MgSO4 and evaporate the solvent to obtain the title compound. m.p. 75°-78° C. Rf (silica gel; 5% EtOAc in hexane)=0.3; IR 2240 cm-1 ; 1730 cm-1.

Workup

  1. customRemove the DMF in vacuo
  2. custompartition the resultant residue between ethyl acetate and water
  3. washWash the organic layer successively with cold 0.5 N aqueous HCl, water, 5% aqueous NaHC03 and brine
  4. dry with materialDry the organic layer over MgSO4
  5. customevaporate the solvent

Sources & evidence

ORD record
ord-3a3d30f66e2a4a77b8d2ec22ad808e8f
Source dataset
uspto-grants-1987_01
Patent number
US04634689

Reaction notes

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