Diethylether water → Ethyl 4-(4-cyano-3-hydroxyphenyl)butanoate

HRID 1937778Notes

Reaction equation

HRID 1937778 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][C:4]=1[O:17]C(C)(C)C)#[N:2].CCOCC.O>C(#N)C.Cl.C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][C:4]=1[OH:17])#[N:2]

Participants

6

Reactant 2

HCID 21584184Diethylether waterHCID 22461662Ethyl 4-(4-cyano-3-t-butoxyphenyl)butanoate

Product 1

HCID 22461711Ethyl 4-(4-cyano-3-hydroxyphenyl)butanoateYield 82.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-(4-cyano-3-t-butoxyphenyl)butanoate (6.8 g, 23.5 mmol) was dissolved in a mixture of acetonitrile (42 mL) and conc. HCl (3.85 mL) and allowed to stand for 80 min. The reaction was poured into ether/water and the ether layer separated. The ether layer was washed with water and brine, and the combined aqueous washes were reextracted once with ether. The combined ether layers were dried over sodium sulfate and concentrated to give 5.1 g of an off white waxy solid. This material was loaded onto a silica gel column (5×15 cm) in CHCl3 and eluted with 20% EtOAc in CHCl3 to yield 4.5 g of ethyl 4-(4-cyano-3-hydroxyphenyl)butanoate: 1H-NMR (CDCl3) 8.2 (1H, s), 7.42 (1H, d), 6.95 (1H, s), 6.77 (1H, d), 4.2 (2H, q), 2.63 (2H, dd), 2.39 (2H, dd), 1.96 (2H, m), 1.28 (3H, t); 13C (CDCl3) 174.4, 159.5, 149.2, 132.8, 120.8, 117.0, 116.1, 97.1, 60.9, 35.2, 33.6, 25.7. 14.1.

Workup

  1. customthe ether layer separated
  2. washThe ether layer was washed with water and brine
  3. dry with materialThe combined ether layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give 5.1 g of an off white waxy solid
  6. washeluted with 20% EtOAc in CHCl3

Sources & evidence

ORD record
ord-2e952a669d914f9aa73ce36d19ef15e1
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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