Water → 6-hydroxychroman-2-carboxylic Acid

HRID 278452Notes

Reaction equation

HRID 278452 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:13]([OH:15])=[O:14])[CH2:7][CH2:6]2.Cl.[NH+]1C=CC=CC=1.O>CCOC(C)=O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:13]([OH:15])=[O:14])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 21584435Pyridinium hydrochlorideHCID 226283666-Methoxychroman-2-carboxylic acid

Product 1

HCID 114241016-hydroxychroman-2-carboxylic AcidYield 90.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(RS)-6-Methoxy-chroman-2-carboxylic acid (1.12 g, 5.37 mmol) and pyridinium hydrochloride (11.2 g, 96.6 mmol) were heated together at 180° C. for 2 hr under argon with stirring. After cooling to ambient temperature H2O (100 ml) and EtOAc (50 ml) was added and shaken. The aqueous phase was extracted with EtOAc (50 ml) and the combined organic extracts were washed with satd. NaCl solution (50 ml) and then dried with Na2SO4 and evaporated to afford (RS)-6-hydroxy-chroman-2-carboxylic acid as white crystals (0.94 g, 4.84 mmol, 90%) Mp. 175-177° C., MS m/e=194.1 (M+).

Workup

  1. additionwas added
  2. stirringshaken
  3. extractionThe aqueous phase was extracted with EtOAc (50 ml)
  4. washthe combined organic extracts were washed with satd
  5. dry with materialNaCl solution (50 ml) and then dried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-f319c509d53e4d048b1bd820c83a907c
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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