Water → 2-Benzyloxy-5-(2-methoxymethoxyethyl)benzamide

HRID 1862620Notes

Reaction equation

HRID 1862620 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][CH2:21][O:22][CH3:23])=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:26]1C=CN=C1)=O.[OH-].[NH4+].O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][CH2:21][O:22][CH3:23])=[CH:14][C:10]=1[C:11]([NH2:26])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 186201312-Benzyloxy-5-(2-methoxymethoxyethyl)benzoic acid

Product 1

HCID 186201822-Benzyloxy-5-(2-methoxymethoxyethyl)benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-benzyloxy-5-(2-methoxymethoxyethyl)benzoic acid (900 mg) in tetrahydrofuran (25 ml) was added 1,1′-carbonyldiimidazole (507 mg) at room temperature, and the mixture was stirred for 1 hour. To the reaction mixture was added 28% ammonium hydroxide (3 ml), and the resulting mixture was stirred for 30 minutes at room temperature. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, crystallization of the residue from hexane and diethyl ether (1/1) gave 2-benzyloxy-5-(2-methoxymethoxyethyl)benzamide (700 mg).

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes at room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was removed under reduced pressure, crystallization of the residue from hexane and diethyl ether (1/1)

Sources & evidence

ORD record
ord-5e66a412ccaf4bc9b0a727b0a7e73ec7
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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