Hydrochloric Acid → HCID 12812407, compound

HRID 848189Notes

Reaction equation

HRID 848189 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([C:8]([CH3:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])[CH:7]=1.[NH2-].[Na+].Cl[C:21](Cl)([CH3:25])[C:22]([O-:24])=[O:23].[Na+].Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:17][C:21]([CH3:25])([C:22]([OH:24])=[O:23])[O:9][C:8]([CH3:16])([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24533Sodium amideHCID 516892Sodium BicarbonateHCID 517058Dalapon-sodiumHCID 12812396HCID 12812396, compound

Product 1

HCID 12812407HCID 12812407, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A dispersion of 24.9 g of 5-chloro-2-hydroxy-α-methyl-α-phenyl-benzenemethanol in 250 ml of toluene was added dropwise with stirring to a mixture of 8 g of sodium amide in 100 ml of toluene and the mixture was refluxed for 6 hours and was then cooled to room temperature. 17 g of sodium dichloropropionate were added thereto in small portions and the mixture was refluxed for 6 hours and was then cooled to room temperature. 700 ml of water were added thereto and the mixture was acidified with N hydrochloric acid solution. The mixture was made alkaline again with a saturated sodium bicarbonate solution and the aqueous phase was washed 3 times with 100 ml of ether and was acidified with 2 N hydrochloric acid. The aqueous phase was extracted 3 times with 100 ml of ether and the combined organic phases were washed 3 times with 80 ml of water, dried over magnesium sulfate and evaporated to dryness under reduced pressure to obtain 23 g of 6-chloro-2,4-dimethyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid (mixture of two racemates diastereoisomers) melting at 181° C.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperaturein small portions and the mixture was refluxed for 6 hours
  3. temperaturewas then cooled to room temperature
  4. washthe aqueous phase was washed 3 times with 100 ml of ether
  5. extractionThe aqueous phase was extracted 3 times with 100 ml of ether
  6. washthe combined organic phases were washed 3 times with 80 ml of water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2f94cedfd10d4ea4bd596d71b3961f57
Source dataset
uspto-grants-1981_10
Patent number
US04294845

Reaction notes

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