Formaldehyde → 3-Hydroxy-2,2-diphenylpropanenitrile

HRID 1685306Notes

Reaction equation

HRID 1685306 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]=[O:17]>N1C=CC=CC=1.O>[OH:17][CH2:16][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]#[N:9]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 6837Diphenylacetonitrile

Product 1

HCID 202707253-Hydroxy-2,2-diphenylpropanenitrileYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
23 °C

Procedure

To a suspension of 2,2-diphenylacetonitrile (2.0 g, 10.35 mmol) and paraformaldehyde (1.242 g, 41.399 mmol) in pyridine (18 mL) was added Triton B (40% solution in water, 1.022 mL, 2.587 mmol) at 0° C. The suspension instantaneously changed color. The cooling bath was removed and the reaction was stirred at 23° C. for ˜40 hours. The reaction was then acidified with acetic acid (2 mL) and poured into water (150 mL). The aqueous phase was extracted with diethyl ether (2×) and the combined organic extracts were washed with water (2×), 1N HCl (2×) and saturated sodium bicarbonate. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified on silica gel Biotage chromatography (ethyl acetate/hexane 10% to 50%) to give the title material (1.83 g, 100%) as an oil. HPLC ret. time (Condition A): 1.682 min. 1H NMR (400 MHz, CDCl3) δ ppm: 2.21 (1H, t, J=7.20 Hz), 4.37 (2H, d, J=6.82 Hz), 7.35-7.44 (10H, m).

Workup

  1. customThe cooling bath was removed
  2. additionpoured into water (150 mL)
  3. extractionThe aqueous phase was extracted with diethyl ether (2×)
  4. washthe combined organic extracts were washed with water (2×), 1N HCl (2×) and saturated sodium bicarbonate
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel Biotage chromatography (ethyl acetate/hexane 10% to 50%)

Sources & evidence

ORD record
ord-393e98bc03cb48b7a81e17095bc9e706
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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