Hydrochloric Acid → HCID 23111659, compound

HRID 1163279Notes

Reaction equation

HRID 1163279 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:24]=O)=[C:13]([CH:23]=1)[O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl>C(=O)(OCC)OCC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:24]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:15][O:14][C:13]=2[CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23111765HCID 23111765, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23111659HCID 23111659, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 7766Diethyl CarbonateSolvent

Procedure

Ethyl 4-[5-(benzyloxy)-2-formylphenoxy]butyrate (8.2 g) was dissolved in diethyl carbonate (100 mL), and potassium t-butoxide (4 g) was added, and the mixture was stirred overnight at room temperature. 1 M hydrochloric acid was added, and the mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. The solvent was evaporated to give the title compound (5.2 g) as crude crystals. A part thereof was recrystallized from ethyl acetate-hexane to give crystals.

Workup

  1. concentrationthe mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bc374278b72f443aa196da4fc1aef910
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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