Gamma-Butyrolactone → HCID 70588848, compound

HRID 2049900Notes

Reaction equation

HRID 2049900 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:7]=3[O:8][C:4]=2[CH:3]=1.[C:16]1(=[O:21])[O:20][CH2:19][CH2:18][CH2:17]1.[H-].[Na+].[H][H]>>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH:12]=[C:11]([O:13][CH:17]([CH2:18][CH3:19])[C:16]([OH:21])=[O:20])[CH:10]=[CH:9][C:7]=3[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 7302Gamma-ButyrolactoneHCID 24758Sodium hydrideHCID 119541287-Chloro-2-dibenzofuranolHCID 178418361HCID 178418361, compound

Product 1

HCID 70588848HCID 70588848, compound

Conditions

Temperature
120 °C

Procedure

110 g (0.5 mole) 7-Chloro-2-hydroxydibenzofuran is dissolved in 200 g (2.3 mole) of butyrolactone. To this solution is added 27.5 g (0.57 mole) sodium hydride 50% dispersion in oil (prewashed with petroleum ether) in small increments. When hydrogen evolution ceases the solution is heated to 120° C. for 2 hours. The excess butyrolactone was distilled off under high vacuum. The crude product was dissolved in water and precipitated into dilute acid. The product was filtered and redissolved in sodium bicarbonate solution. The solution was charcoal treated and precipitated in dilute acid filtered and dried. 137 g., m.p. 143°-145° C. were obtained. This Example corresponds to Example 69 in Table I.

Workup

  1. distillationThe excess butyrolactone was distilled off under high vacuum
  2. dissolutionThe crude product was dissolved in water
  3. customprecipitated
  4. additioninto dilute acid
  5. filtrationThe product was filtered
  6. dissolutionredissolved in sodium bicarbonate solution
  7. additiontreated
  8. customprecipitated in dilute acid
  9. filtrationfiltered
  10. customdried
  11. custom, m.p. 143°-145° C. were obtained

Sources & evidence

ORD record
ord-ccb495ce9ea84e39b3a7e43de3f8a3b4
Source dataset
uspto-grants-1980_04
Patent number
US04199346

Reaction notes

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