Dichloroacetic Acid → HCID 21163202, compound

HRID 1278289Notes

Reaction equation

HRID 1278289 reaction equation
Cl[CH:2](Cl)[C:3]([OH:5])=[O:4].[H-].[Na+].[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([OH:25])=[C:14]([C:16]([CH3:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:17])[CH:15]=1>O1CCOCC1>[CH3:24][C:16]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:14]2[CH:15]=[C:10]([CH3:9])[CH:11]=[CH:12][C:13]=2[O:25][CH:2]([C:3]([OH:5])=[O:4])[O:17]1

Participants

5

Reactant 3

HCID 6597Dichloroacetic AcidHCID 24758Sodium hydrideHCID 13076847HCID 13076847, compound

Product 1

HCID 21163202HCID 21163202, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
90 °C

Procedure

A solution of 13 ml of dichloroacetic acid and 75 ml of dioxane was added over 40 minutes to a suspension of 1.6 g of dibenzo-18-courone-6, 20.2 g of sodium hydride as a 50% oil suspension and 250 ml of dioxane and then a solution of 30 g of the product of Step A in 150 ml of dioxane was added thereto at 60° C. over one hour. The mixture was heated at 90° C. for 2 hours, was cooled and poured into 500 ml of ice. The aqueous phase was washed 3 times with 300 ml of ether, was acidified with concentrated hydrochloric acid and was extracted 3 times with 300 ml of ether. The ether phase was extracted 4 times with 100 ml of aqueous sodium bicarbonate solution and the combined aqueous phase was acidified with hydrochloric acid and was extracted 3 times with 300 ml of ether. The ether phase was washed with water until the wash water was neutral, dried over magnesium sulfate and was evaporated to dryness under reduced pressure to obtain 28 g of raw 4,6-dimethyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid (mixture of 2 diastereoisomeric racemates).

Workup

  1. temperaturewas cooled
  2. washThe aqueous phase was washed 3 times with 300 ml of ether
  3. extractionwas extracted 3 times with 300 ml of ether
  4. extractionThe ether phase was extracted 4 times with 100 ml of aqueous sodium bicarbonate solution
  5. extractionwas extracted 3 times with 300 ml of ether
  6. washThe ether phase was washed with water until the wash water
  7. dry with materialdried over magnesium sulfate
  8. customwas evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-87ec8c50963c44a3a6f95341fe2dde7a
Source dataset
uspto-grants-1981_07
Patent number
US04281012

Reaction notes

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