Acetic Acid → HCID 20450186, compound

HRID 358163Notes

Reaction equation

HRID 358163 reaction equation
C1O[C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:8][CH:7]=2)([CH3:5])[O:3]C1.C(O)(=O)C.O.[OH-].[Na+]>CO>[C:14]([NH:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][CH:8]=1)([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 56636050HCID 56636050, compound

Product 1

HCID 20450186HCID 20450186, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

125 g of N-BOC-p-aminomethylacetophenone ethylene ketal are heated for 15 minutes at 65° in 250 ml of methanol and 250 ml of acetic acid as well as 50 ml of water. The reaction mixture is cooled to 0°, adjusted to a pH of 10 with 10N aqueous NaOH, extracted with ethyl acetate and washed neutral with saturated aqueous NaCl solution. The crude product obtained after drying and concentrating by evaporation is crystallised from hexane. N-BOC-p-aminomethylacetophenone having a melting point of 73°-75° is obtained. IR: 3420, 1707, 1680, 1607, 1500 cm-1 (CH2Cl2). UV: 250 nm (15700) in C2H5OH.

Workup

  1. temperatureThe reaction mixture is cooled to 0°
  2. extractionextracted with ethyl acetate
  3. washwashed neutral with saturated aqueous NaCl solution
  4. customThe crude product obtained
  5. customafter drying
  6. concentrationconcentrating by evaporation
  7. customis crystallised from hexane

Sources & evidence

ORD record
ord-5a7852108a2d4bd8a5bbb343c3cdd092
Source dataset
uspto-grants-1984_08
Patent number
US04464366

Reaction notes

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