Hydrochloric Acid → 2,3-dihydro-1,4-benzodioxin-2-one

HRID 569230Notes

Reaction equation

HRID 569230 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9](=[O:12])[CH2:10]Cl.[H-].[Na+].Cl.C(OCC)C>CN(C)C=O>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1][CH2:10][C:9]1=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 14124714Norepinephrine Impurity 7

Product 1

HCID 46854502,3-dihydro-1,4-benzodioxin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

161.5 g (0.87 mole) of chloroacetic acid 2-hydroxyphenyl ester were dissolved in 300 ml of anhydrous dimethylformamide. 20.88 g (0.87 mole) of sodium hydride were added portion by portion with indirect ice refrigeration. After the ending of the addition, heating was carried out for 3 hours at 35° C. followed by hydrolysis in which the reaction mixture was distributed between 600 ml 1N hydrochloric acid and 600 ml diethyl ether. The organic phase was dried with sodium sulfate and was concentrated by evaporation. 117.6 g (90% of the theoretical amount) of raw 3-H-benzo-1,4-dioxin-2-one were obtained. The light-brown oil which was accumulated at first was crystallized in the course of time (melting point 45°-53° C.2).

Workup

  1. additionAfter the ending of the addition
  2. temperatureheating
  3. customfollowed by hydrolysis in which the reaction mixture
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationwas concentrated by evaporation

Sources & evidence

ORD record
ord-5caa902c6a374d7198bbfddeea01b29e
Source dataset
uspto-grants-1988_03
Patent number
US04731466

Reaction notes

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