Hydrochloric Acid → HCID 9855924, compound

HRID 983661Notes

Reaction equation

HRID 983661 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=O)[CH3:2].[O-]CC.[Na+].Cl>C(=O)(OCC)OCC.C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]=1)=[O:17])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 11390709Ethyl 4-(2-formylphenoxy)butyrate

Product 1

HCID 9855924HCID 9855924, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7766Diethyl CarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(2-formylphenoxy)butyric acid ethylester (2.4 g) in diethyl carbonate (24 ml), a solution of 20% sodium ethoxide in ethanol (4.1 g) was added at room temperature, and the solution was stirred at 50° C. for 1 hour. The solution was allowed to cool to room temperature, and neutralized with 1N hydrochloric acid. After ethyl acetate extraction, the organic layer was washed with saturated salt water, dried over anhydrous sodium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) and concentration of the appropriate eluate gave colorless oil of 2,3-dihydro-1-benzoxepin-4-carboxylic acid ethylester (1.3 g, yield 61%).

Workup

  1. temperatureto cool to room temperature
  2. extractionAfter ethyl acetate extraction
  3. washthe organic layer was washed with saturated salt water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) and concentration of the appropriate eluate

Sources & evidence

ORD record
ord-02706003f07e473881ee5994f8c05a26
Source dataset
uspto-grants-2005_03
Patent number
US06864367B2

Reaction notes

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