Hydrochloric Acid → 3-Hydroxy-4-propoxybenzonitrile

HRID 1246596Notes

Reaction equation

HRID 1246596 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:14]=C(O)C=1)[C:12]#[N:13])C1C=CC=CC=1.B.[CH2:19]1[CH2:23][O:22][CH2:21][CH2:20]1.Cl.[C:25]([O-])(O)=O.[Na+]>C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:19][C:23]=1[O:22][CH2:21][CH2:20][CH3:25])[C:12]#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 219043673-Benzyloxy-5-hydroxybenzonitrile

Product 1

HCID 219043603-Hydroxy-4-propoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-benzyloxy-5-hydroxybenzonitrile (225 mg, 1 mmol) was dissolved in 2 mL THF. 2 mL of BH3-THF (1.5 M in THF and ether) was added dropwise, then the mixture was heated at reflux temperature for 3 hours. After cooling, the mixture was carefully poured to 3M HCl (ice cooled) and allowed to stir for 20 hours at room temperature. The mixture was neutralized with solid NaHCO3, thus the product precipitated as a white solid. The product was collected by filtration, washed with water, and dried (140 mg, 61%): MP 164–166° C. (dec); 1H NMR (DMSO-d6, 400 MHz) δ9.28 (br, 1H), 7.41 (d, 2H, J=6.9 Hz), 7.36 (dd, 2H, J=7.0 and 7.6 Hz), 7.30 (dd, 1H, J=7.0 and 6.6 Hz), 6.43 (s, 1H), 6.32 (s, 1H), 6.21 (dd, 1H, J=2.2 and 2.0 Hz), 4.99 (S, 2H), 3.57 (S, 2H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 3 hours
  3. temperatureAfter cooling
  4. customthus the product precipitated as a white solid
  5. filtrationThe product was collected by filtration
  6. washwashed with water
  7. customdried (140 mg, 61%)

Sources & evidence

ORD record
ord-d5097f02d7c44d2ba6a776ead796b4ca
Source dataset
uspto-grants-2006_10
Patent number
US07129225B2

Reaction notes

Loading…