Water → HCID 12769820, compound

HRID 26687Notes

Reaction equation

HRID 26687 reaction equation
[CH2:1]([CH:3]1[CH:8]([CH3:9])[C:7](=[O:10])[C:6]2[CH:11]=[C:12]([CH:15]([CH3:20])[C:16]([O:18]C)=[O:17])[CH:13]=[CH:14][C:5]=2[O:4]1)[CH3:2].C(=O)(O)[O-].[Na+].O>C(O)C>[CH2:1]([CH:3]1[CH:8]([CH3:9])[C:7](=[O:10])[C:6]2[CH:11]=[C:12]([CH:15]([CH3:20])[C:16]([OH:18])=[O:17])[CH:13]=[CH:14][C:5]=2[O:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21322013Methyl 2-[2,3-dihydro-2-ethyl-3-methyl-4-oxo-4H-1-benzopyran-6-yl]propionate

Product 1

HCID 12769820HCID 12769820, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-[2,3-dihydro-2-ethyl-3-methyl-4-oxo-4H-1-benzopyran-6-yl]propionate (6 g) was dissolved in ethanol (200 ml) and heated to reflux with dilute aqueous sodium bicarbonate solution (50 ml) for eight hours. The reaction mixture was poured into water, acidified and extracted with ether. The combined etheral extracts were washed with water and dried (MgSO4) and concentrated in vacuo affording a mixture of the desired product and starting material which were separated by chromatography on silica gel using dichloromethane/ether mixtures as eluant. The title compound was recrystallised from petroleum ether (bp 40°-60° C.) as a white solid: 1.4 g, mp 114°-115° C.

Workup

  1. temperatureheated
  2. extractionextracted with ether
  3. washThe combined etheral extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customaffording

Sources & evidence

ORD record
ord-c6d54deac7e142829d3b2da97761ea92
Source dataset
uspto-grants-1979_04
Patent number
US04151179

Reaction notes

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