Sodium Bicarbonate → HCID 14277778, compound

HRID 484020Notes

Reaction equation

HRID 484020 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH:14]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].C(=O)(O)[O-].[Na+]>Br>[CH3:13][C:5]1[C:6](=[O:11])[C:7]([CH3:10])=[C:8]([CH3:9])[C:3](=[O:2])[C:4]=1[CH:14]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 14576260HCID 14576260, compound

Product 1

HCID 14277778HCID 14277778, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-7-(3-pyridyl)heptanoic acid (1.0 g, 2.6 mmol) prepared in the Reference Example 11 was dissolved in 47% aqueous hydrogen bromide (5 ml) and the solution was heated at a reflux temperature for 2 hours. After the reaction was completed, the reaction mixture was cooled. The solution was made alkaline with sodium bicarbonate and the product was extracted with ethylacetate. The extract was washed with water, dried, and evaporated in vacuo. The resulting hydroquinone was oxidized with air and the solvent was evaporated to yield 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-(3-pyridyl)heptanoic acid (0.8 g, 86.8%) after crystallization from ethylacetate, m.p. 126°-127° C.

Workup

  1. temperaturethe solution was heated at a reflux temperature for 2 hours
  2. temperaturethe reaction mixture was cooled
  3. extractionthe product was extracted with ethylacetate
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated in vacuo
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-17955112a42d4c22a3f75be8041a81ad
Source dataset
uspto-grants-1993_07
Patent number
US05229385

Reaction notes

Loading…