Hydrochloric Acid → Benzyl 2-benzyloxy-5-cyanobenzoate

HRID 644400Notes

Reaction equation

HRID 644400 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[C:10]1[CH:15]=[C:14]([CH:16]=O)[CH:13]=[CH:12][C:11]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO.C[N:31]1CCCC1=O.Cl>O>[CH2:1]([O:8][C:9](=[O:26])[C:10]1[CH:15]=[C:14]([C:16]#[N:31])[CH:13]=[CH:12][C:11]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 443297Hydroxyamine hydrochlorideHCID 10405334Benzyl 2-benzyloxy-5-formylbenzoate

Product 1

HCID 18974028Benzyl 2-benzyloxy-5-cyanobenzoateYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-benzyloxy-5-formylbenzoic acid benzyl ester (693 mg, 2 mmol), hydroxylamine hydrochloride (167 mg, 2.4 mmol), and N-methylpyrrolidone (3 mL) was stirred at 115□ for 4 hours. After the reaction mixture was cooled, 2N hydrochloric acid (5 mL) and water (30 mL) were added and the mixture was extracted with ethyl acetate. The organic layer was washed with 2N aqueous sodium hydroxide, water, and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was suspended and washed with isopropyl ether under heating at reflux to give the title compound (527 mg, 76.7%) as a white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 2N aqueous sodium hydroxide, water, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. washwashed with isopropyl ether
  7. temperatureunder heating
  8. temperatureat reflux

Sources & evidence

ORD record
ord-8f6971dc03a5490c9bc034032685815f
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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