Sodium Hydroxide → 8-Methoxychroman-2-carboxylic acid

HRID 1720345Notes

Reaction equation

HRID 1720345 reaction equation
C([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:16][CH3:17])[CH:10]=[CH:11][CH:12]=2)[O:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:17][O:16][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[O:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18787171Ethyl 8-methoxy-chroman-2-carboxylate

Product 1

HCID 152291968-Methoxychroman-2-carboxylic acidYield 106.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 100.7 g (0.43 mol) 8-methoxy-2-chromancarboxylic acid ethyl ester and 20.1 g (0.50 mol) sodium hydroxide in 800 ml ethanol was stirred for 24 h at 20°. After evaporation, the residue was treated with water and extracted with diethyl ether. The aqueous phase was acidified and then extracted with diethylether. Usual work-up yielded 95.2 g of crystalline 8-methoxychroman-2-carboxylic acid.

Workup

  1. customAfter evaporation
  2. additionthe residue was treated with water
  3. extractionextracted with diethyl ether
  4. extractionextracted with diethylether

Sources & evidence

ORD record
ord-4bd69051d8c546f49c055270fc8434a8
Source dataset
uspto-grants-1996_04
Patent number
US05506246

Reaction notes

Loading…