Benzyltrimethylammonium hydroxide → 6-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxo-4H-1-benzopyran-2-carboxylic acid

HRID 435857Notes

Reaction equation

HRID 435857 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][CH2:13][CH3:14])[CH2:2]1.[OH:15][C:16]1[CH:17]=[CH:18][C:19]2[O:24][C:23]([C:25]([O:27]CC)=[O:26])=[CH:22][C:21](=[O:30])[C:20]=2[CH:31]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)C.O.CN(C)C=O>[OH:1][CH:3]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][CH3:14])[CH2:2][O:15][C:16]1[CH:17]=[CH:18][C:19]2[O:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][C:21](=[O:30])[C:20]=2[CH:31]=1

Participants

8

Reactant 4

HCID 66854Benzyltrimethylammonium hydroxideHCID 516892Sodium BicarbonateHCID 6164644H-1-Benzopyran-2-carboxylic acid, 6-hydroxy-4-oxo-, ethyl esterHCID 123558511,2-Epoxy-3-(2-propylphenoxy)propane

Product 1

HCID 130909986-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxo-4H-1-benzopyran-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 19.2 parts of 1,2-epoxy-3-(2-propylphenoxy) propane, 23.4 parts of ethyl 6-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate and 0.1 parts of benzyl trimethylammonium hydroxide in 50 parts of dimethyl formamide was heated under reflux for 3 hours. The solvent was evaporated under reduced pressure and the oil remaining dissolved in ethyl acetate. The solution was washed with dilute sodium hydroxide and water, dried over magnesium sulphate, filtered and evaporated to leave an oil. The oil was dissolved in ethyl alcohol, 20.0 parts of sodium bicarbonate were added, and the mixture was boiled for 2 hours, during which time water was added and the ethyl alcohol allowed to boil off. The aqueous solution was washed with ethyl acetate and acidified with dilute hydrochloric acid to give a brown precipitate which was collected and crystallised twice from ethyl alcohol to yield 10.5 parts of 6-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxo-4H-1-benzopyran-2-carboxylic acid, melting point 164°-166° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe oil remaining dissolved in ethyl acetate
  5. washThe solution was washed with dilute sodium hydroxide and water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto leave an oil
  10. additionwas added
  11. washThe aqueous solution was washed with ethyl acetate
  12. customto give a brown precipitate which
  13. customwas collected
  14. customcrystallised twice from ethyl alcohol

Sources & evidence

ORD record
ord-6b16b91801814526ac9e6f27c279cc31
Source dataset
uspto-grants-1977_02
Patent number
US04006245

Reaction notes

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