Benzene → 1,3-Benzodioxole-2-acetic acid, 2-phenyl-

HRID 918102Notes

Reaction equation

HRID 918102 reaction equation
[Mg].II.[C:4]1([CH:10]2[O:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18](CCBr)[C:12]=3[O:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:22](=[O:24])=[O:23].[CH:25]1C=CC=CC=1>CCOCC>[C:4]1([C:10]2([CH2:25][C:22]([OH:24])=[O:23])[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[O:14]2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 241BenzeneHCID 280Carbon DioxideHCID 807IodineHCID 5462224MagnesiumHCID 68135680HCID 68135680, compound

Product 1

HCID 307981,3-Benzodioxole-2-acetic acid, 2-phenyl-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 0.61 g. of magnesium, in chips, 10 cc. of anhydrous ether and one crystal of iodine, one cc. of a solution of 7.3 g. of 2-phenyl-2-bromoethyl-1,3-benzodioxole in 25 cc. of anhydrous ether is added. When the reaction has begun, the mixture is stirred and the rest of the mixture is then added dropwise. The mixture is then refluxed for 2 hours. After cooling CO2 is bubbled into the reaction mixture for 2 hours. The mixture is then cooled with ice and hydrolysed with 25% H2SO4. The ether phase is then separated and dried with Na2SO4. After evaporation, the product obtained has the m.p. 152°-53°C. (from benzene).

Workup

  1. additionTo a mixture of 0.61 g
  2. additionthe rest of the mixture is then added dropwise
  3. temperatureThe mixture is then refluxed for 2 hours
  4. customis bubbled into the reaction mixture for 2 hours
  5. temperatureThe mixture is then cooled with ice and hydrolysed with 25% H2SO4
  6. customThe ether phase is then separated
  7. dry with materialdried with Na2SO4
  8. customAfter evaporation
  9. customthe product obtained

Sources & evidence

ORD record
ord-6e209cdd3fea4f5985da150caa00da9b
Source dataset
uspto-grants-1976_07
Patent number
US03969368

Reaction notes

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