Hydrochloric Acid → HCID 15613920, compound

HRID 2351532Notes

Reaction equation

HRID 2351532 reaction equation
[CH3:1][C:2]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]([OH:15])=[O:14])[CH:8]=2)[O:3]1.[CH3:27]O.Cl>O1CCOCC1>[CH3:1][C:2]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]([O:15][CH3:27])=[O:14])[CH:8]=2)[O:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 15613919HCID 15613919, compound

Product 1

HCID 15613920HCID 15613920, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 22 g of 2-methyl-2-(4-nitrophenoxymethyl)-4-oxochroman-6-carboxylic acid (prepared as described in Preparation 42), 100 ml of methanol and 200 ml of a 4N solution of hydrogen chloride in dioxane was allowed to stand overnight at room temperature. At the end of this time, the solvent was stripped from the reaction mixture by evaporation under reduced pressure. The residue was then dissolved in benzene, and the resulting solution was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, eluted with a 20:1 by volume mixture of benzene and ethyl acetate, to afford 16.1 g of the title compound, melting at 144°-145° C.

Workup

  1. customAt the end of this time, the solvent was stripped from the reaction mixture by evaporation under reduced pressure
  2. dissolutionThe residue was then dissolved in benzene
  3. washthe resulting solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. washeluted with a 20:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-16cbc34123f949958df515dd00da12b1
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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