Hydrochloric Acid → HCID 54298459, compound

HRID 423262Notes

Reaction equation

HRID 423262 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11]COC)=[C:6]([O:15][CH3:16])[CH:5]=1.Cl>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([O:15][CH3:16])[CH:5]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58629777HCID 58629777, compound

Product 1

HCID 54298459HCID 54298459, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methoxy-4-methoxymethoxy-5-methylbenzoic acid methyl ester (650 mg) in THF (5 mL) was added 6N-hydrochloric acid (5 mL), and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1, v/v) to give the title compound (365 mg).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-6aba6d8b2a5946dea3097d1ac2bab144
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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