Sodium Hydroxide → HCID 18472313, compound

HRID 566016Notes

Reaction equation

HRID 566016 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:16][CH:15]([CH3:17])[C:14]([C:18]([O:20]CC)=[O:19])=[CH:13][C:12]=3[CH:23]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:16][CH:15]([CH3:17])[C:14]([C:18]([OH:20])=[O:19])=[CH:13][C:12]=3[CH:23]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18472643HCID 18472643, compound

Product 1

HCID 18472313HCID 18472313, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of ethyl 6-(4-methylphenyl)-2-methyl-2H-1-benzopyran-3-carboxylate (3.0 g) in ethanol-tetrahydrofuran (30-30 ml) was added 1N sodium hydroxide (12 ml) at room temperature, and the mixture was stirred for 16 hours. Under reduced pressure, the solvent was evaporated and acidified with 1N hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 6-(4-methylphenyl)-2-methyl-2H-1-benzopyran-3-carboxylic acid (2.15 g) as yellow crystals.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-b8cc8104b5394b1eb6798a0b7bfa79f9
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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