Sodium Hydroxide → HCID 20095707, compound

HRID 248550Notes

Reaction equation

HRID 248550 reaction equation
Br[C:2]1[C:10]([O:11][CH2:12][CH3:13])=[C:9]([O:14][CH3:15])[C:8]([O:16][CH2:17][CH3:18])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-:19].[Na+]>O.[Cu]>[CH2:12]([O:11][C:10]1[C:2]([OH:19])=[C:3]([CH:7]=[C:8]([O:16][CH2:17][CH3:18])[C:9]=1[O:14][CH3:15])[C:4]([OH:6])=[O:5])[CH3:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20095716HCID 20095716, compound

Product 1

HCID 20095707HCID 20095707, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

68 g of 2-bromo-3,5-diethoxy-4-methoxybenzoic acid prepared in Referential Example 4 was suspended in 260 ml of water and 32 g of caustic soda and 0.88 g of copper powder were added thereto. The mixture was heated at 120° C. for 3 hr while stirring, and then cooled. Carbon was added thereto, and the mixture was filtered through Celite. The filtrate was neutralized with 140 ml of 6 N hydrochloric acid and 1 l of chloroform was added thereto. The mixture was subjected to liquid-liquid separation. The organic phase was washed with water, dried and then concentrated to prepare 53 g of the crude product (ocherous solid).

Workup

  1. temperaturecooled
  2. additionCarbon was added
  3. filtrationthe mixture was filtered through Celite
  4. additionwas added
  5. customThe mixture was subjected to liquid-liquid separation
  6. washThe organic phase was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto prepare 53 g of the crude product (ocherous solid)

Sources & evidence

ORD record
ord-d59cb3f4a4fb4798abeaa39b86e2c2e1
Source dataset
uspto-grants-1993_05
Patent number
US05210239

Reaction notes

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