Carbon Dioxide → 174186-43-7

HRID 342419Notes

Reaction equation

HRID 342419 reaction equation
[Mg].Br[C:3]1[C:11]2[O:10][C:9]3[CH2:12][CH2:13][CH2:14][CH2:15][C:8]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:16](=[O:18])=[O:17].Cl>O1CCCC1.C(Cl)(Cl)Cl>[CH2:15]1[C:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([C:16]([OH:18])=[O:17])[C:11]=3[O:10][C:9]=2[CH2:12][CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 54255872HCID 54255872, compound

Product 1

HCID 19576778174186-43-7Yield 89.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

To a suspension of magnesium (345 mg) in tetrahydrofuran (5 ml) was added 6-bromo-1,2,3,4-tetrahydrodibenzofuran (3.39 g) in tetrahydrofuran (15 ml) dropwise. The mixture was refluxed for 1 hour and cooled to 4° C. Dry ice (2.7 g) was added to the mixture and the mixture was stirred at ambient temperature for 30 minutes. To the mixture was added 3.6% hydrochloric acid and chloroform. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from n-hexane to give 1,2,3,4-tetrahydrodibenzofuran-6-carboxylic acid (2.60 g).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-a9e838dc8dae45ba9c40c823a9275570
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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