Benzyl Chloride → Benzyl 2-acetamido-4-(benzyloxy)benzoate

HRID 1271211Notes

Reaction equation

HRID 1271211 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:15]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:12]([O:14][CH2:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:5]=2)=[CH:13][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 184528302-Acetamido-4-hydroxybenzoic acid

Product 1

HCID 69461669Benzyl 2-acetamido-4-(benzyloxy)benzoateYield 178.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1.1 g (5.64 mmol) of 2-acetylamino-4-hydroxy-benzoic acid (preparation: Recl. Trav. Chim. Pays-Bas, 72, p195, 1953), 1.6 ml (13.53 mmol) of benzyl chloride, 3.9 g (28.18 mmol) of potassium carbonate in DMF (15 ml) was stirred at 80° C. for 17 h under argon. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 and water. The layers were separated, the aqueous layer once extracted with CH2Cl2, the organic layers combined, washed with brine, dried over MgSO4 and concentrated in vacuo, to give 1.89 g (85.75%) of the desired 2-acetylamino-4-benzyloxy-benzoic acid benzyl ester as an off-white solid. ISP mass spectrum, m/e: 376.5 (M+1 calculated for C23H21NO4: 375.42).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between CH2Cl2 and water
  3. customThe layers were separated
  4. extractionthe aqueous layer once extracted with CH2Cl2
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4231e404e0c84270bfb6883a1623d8dc
Source dataset
uspto-grants-2007_04
Patent number
US07205309B2

Reaction notes

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