tert-butyl 6-(4-methylphenyl)-2H-1-benzopyran-3-carboxylate → 6-(4-methylphenyl)-2H-1-benzopyran-3-carboxylic acid

HRID 566015Notes

Reaction equation

HRID 566015 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][CH2:15][C:14]([C:17]([O:19]C(C)(C)C)=[O:18])=[CH:13][C:12]=3[CH:24]=2)=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>CCCCCC>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:16][CH2:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:12]=3[CH:24]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10615821tert-butyl 6-(4-methylphenyl)-2H-1-benzopyran-3-carboxylateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 105396746-(4-methylphenyl)-2H-1-benzopyran-3-carboxylic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To tert-butyl 6-(4-methylphenyl)-2H-1-benzopyran-3-carboxylate (3.00 g) was added 4N hydrochloric acid-ethyl acetate (10 ml) at room temperature, and the mixture was stirred for 16 hours. To the reaction mixture was added hexane, and crystal was collected by filtration and washed with hexane to give 6-(4-methylphenyl)-2H-1-benzopyran-3-carboxylic acid (2.14 g) as pale yellow crystals.

Workup

  1. filtrationwas collected by filtration
  2. washwashed with hexane

Sources & evidence

ORD record
ord-fa1c53aa466447c7908ab94db2c6b974
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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