Hydrochloric Acid → Ethyl 2-(3-cyanophenyl)acetate

HRID 526407Notes

Reaction equation

HRID 526407 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][C:13](C)(C)[CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.O1CCOCC1>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 102224183Tert-butyl 2-(3-cyanophenyl)acetate

Product 1

HCID 11194802Ethyl 2-(3-cyanophenyl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combined tert-butyl 2-(3-cyanophenyl)acetate (500 mg, 2.301 mmol), ethanol (10 mL) and 4 N HCl in dioxane (0.288 mL, 1.151 mmol) and the solution heated at 60° C. for 22 h. The solution was concentrated in vacuo to give the title compound a yellow oil which was used without further purification. MS m/z 190 [M+H]+. 1H NMR (400 MHz, chloroform-d) δ ppm 1.23-1.31 (m, 3H) 3.65 (s, 2H) 4.17 (q, J=7.1 Hz, 2H) 7.40-7.47 (m, 1H) 7.51-7.56 (m, 1H) 7.56-7.62 (m, 2H).

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-d2931625785d4446a73dcb0b7ddbd43a
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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