Hydrochloric Acid → [4-(2,4-Dihydroxyphenyl)cyclohexylidene]acetonitrile

HRID 585669Notes

Reaction equation

HRID 585669 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][C:18](=[CH:21][C:22]#[N:23])[CH2:17][CH2:16]1.Cl.C(=O)(O)[O-].[Na+]>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:16][CH2:17][C:18](=[CH:21][C:22]#[N:23])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22337767{4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrile

Product 1

HCID 9964617[4-(2,4-Dihydroxyphenyl)cyclohexylidene]acetonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added (±)-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrile (141 mg, 0.45 mmol) and methanol (5 ml). The reaction mixture was stirred, the solution was heated to reflux temperature and aqueous hydrochloric acid (5 ml, 1.0M) was added slowly. Heating was continued for 1 hr and the reaction mixture was allowed to cool to room temperature prior to the addition of saturated aqueous sodium bicarbonate solution (12 ml). The reaction mixture was then partitioned between ethyl acetate (30 ml) and water (10 ml). The aqueous layer was extracted with ethyl acetate (3×15 ml) and the combined organic layers washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:1, v/v) to afford the title compound as a white solid (90 mg, 88%). m/z (ES−) 228 (M−H+); δH(CD3OD) 1.56-1.68 (2H, m), 2.02-2.14 (2H, m), 2.33-2.48 (2H, m), 2.57 (1H, m), 3.01 (1H, m), 3.14 (1H, m), 5.31 (1H, s), 6.26 and 6.28 (1H, d), 6.32 (1H, d), 6.80 (1H, d).

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. temperaturethe solution was heated
  3. additionwas added slowly
  4. temperatureHeating
  5. customThe reaction mixture was then partitioned between ethyl acetate (30 ml) and water (10 ml)
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×15 ml)
  7. washthe combined organic layers washed with brine (20 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:1

Sources & evidence

ORD record
ord-5c8d7eec7e174f0e931703f6b7fbfed2
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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