Ammonia → HCID 15499742, compound

HRID 581697Notes

Reaction equation

HRID 581697 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15]C.[C:18](Cl)(=[O:20])[CH3:19].N>ClCCl.C.O>[CH3:5][O:6][C:7](=[O:17])[CH2:8][C:9]1[CH:14]=[C:13]([C:18](=[O:20])[CH3:19])[CH:12]=[CH:11][C:10]=1[OH:15]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6367Acetyl chlorideHCID 99590Methyl 2-methoxybenzeneacetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15499742HCID 15499742, compound

Reagents, catalysts & solvents 3

HCID 297MethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of aluminum chloride (35.0 g, 262.5 mmol) in dichloromethane (75 mL) was added a solution of (2-Methoxy-phenyl)-acetic acid methyl ester (13.5 g, 75.0 mmol) and acetyl chloride (5.86 mL, 82.5 mmol)in dichloromethane (75 mL) dropwise. After the addition was complete the reaction was heated to reflux for 5 hours. The reaction mixture was then cooled and carefully poured onto a mixture of ice and water. The aqueous layer was then extracted with ethyl acetate (2×400 mL). The combined extracts were then washed with saturated sodium chloride (1×100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a solid. 1H NMR (400 MHz, DMSO): δ 10.51 (s, 1H), 7.79 (m, 2H), 6.88 (d, 1H), 3.63 (s, 2H), 3.59 (s, 3H), 2.47 (s, 3H). Mass Spectrum (Chemical Ionization, 1% NH3 in CH4) m/z 209 (M+H).

Workup

  1. additionAfter the addition
  2. temperaturewas heated
  3. temperatureto reflux for 5 hours
  4. temperatureThe reaction mixture was then cooled
  5. extractionThe aqueous layer was then extracted with ethyl acetate (2×400 mL)
  6. washThe combined extracts were then washed with saturated sodium chloride (1×100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a solid

Sources & evidence

ORD record
ord-16f7d28dc03f41efbf69ec49f521cf93
Source dataset
uspto-grants-1999_07
Patent number
US05922697

Reaction notes

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