p-Anisoyl chloride → HCID 11470410, compound

HRID 1954445Notes

Reaction equation

HRID 1954445 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH:12]([NH:15][CH:16](O)[CH3:17])([CH3:14])[CH3:13].C1C[O:22]CC1>>[CH:12]([N:15]([CH2:16][CH2:17][OH:22])[C:1](=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8028Tetrahydrofuran2×HCID 20976152HCID 20976152, compound

Product 1

HCID 11470410HCID 11470410, compoundYield 88%

Conditions

Temperature
7 °C

Procedure

Anisoyl chloride (17.1 g, 0.1 mol) in THF (100 mL) was added dropwise to a solution of N-isopropylaminoethanol (41.3 g, 0.4 mol) in THF (200 mL) under magnetic stirring at 4 to 10° C. The reaction mixture was stirred for 2 h at room temperature, and the solvent was evaporated in vacuo. The residue was dissolved in ice-cold water (200 mL), and the solution was neutralized with conc. hydrochloric acid. The emulsion was extracted with ethyl acetate (3' 150 mL). Extracts were washed with saturated aqueous NaCl (3' 50 mL), dried over Na2SO4, and evaporated to a solid. Recrystallization from warm toluene-hexanes gave pure 8 as white crystals (20.5 g, 88%). 1H NMR (CDCl3): 7.32 (2H, d, J=8.6 Hz); 6.89 (2H, d, J=8.6 Hz); 4.40 (1H, br. s); 4.09 (1H, m); 3.80 (3H, s); 3.90-3.70 (1H, m); 3.53 (2H, t, J=4.6 Hz); 1.13 (6H, d, J=6.8 Hz). 13C NMR (CDCl3): 173.56 (C=O); 160.60 (C--OMe); 128.71 [C--C(O)]; 128.16 (Arom. CH); 113.89 (Arom. CH); 63.69 (CH2OH); 55.39 (OCH3); 50.60 (N--CH); 44.45 (N--CH2); 21.19 (C--CH3).

Workup

  1. stirringThe reaction mixture was stirred for 2 h at room temperature
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ice-cold water (200 mL)
  4. extractionThe emulsion was extracted with ethyl acetate (3' 150 mL)
  5. washExtracts were washed with saturated aqueous NaCl (3' 50 mL),
  6. dry with materialdried over Na2SO4
  7. customevaporated to a solid
  8. customRecrystallization
  9. temperaturefrom warm toluene-hexanes

Sources & evidence

ORD record
ord-fe245f3ac5b845ad867241466719334b
Source dataset
uspto-grants-2000_09
Patent number
US06121437

Reaction notes

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