Benzene → 3-hydroxy-4-acetyl-6,6-di-propyl-6H-dibenzo-[b,d]-pyran

HRID 1288327Notes

Reaction equation

HRID 1288327 reaction equation
[CH2:1]([Mg]I)[CH2:2][CH3:3].O[C:7]1[CH:8]=[CH:9][C:10]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=O)[O:12][C:11]=2[C:21]=1[C:22](=[O:24])[CH3:23].[OH2:25].S(=O)(=O)(O)O.[CH:31]1[CH:36]=CC=C[CH:32]=1>CCOCC>[OH:25][C:7]1[CH:8]=[CH:9][C:10]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13]([CH2:32][CH2:31][CH3:36])([CH2:1][CH2:2][CH3:3])[O:12][C:11]=2[C:21]=1[C:22](=[O:24])[CH3:23]

Participants

7

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 1118Sulfuric AcidHCID 215047724-Acetyl-3-hydroxybenzo[c]chromen-6-oneHCID 178455858HCID 178455858, compound

Product 1

HCID 215047553-hydroxy-4-acetyl-6,6-di-propyl-6H-dibenzo-[b,d]-pyranYield 23.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The starting compound was prepared as follows: A solution of 0.3 mol of propyl magnesium iodide in 150 ml of ether was admixed all at once with a suspension of 16.6 gm (0.065 mol) of 3-hydroxy-4-acetyl-6-oxo-6H-dibenzo-[b,d]-pyran (prepared analogous to Example 7) in 300 ml of benzene. The resulting mixture was heated for 3 hours and subsequently decomposed by addition of 500 ml of water containing 25 ml of concentrated sulfuric acid. The organic phase was separated, the aqueous phase was extracted with ether, and the combined extracts were dried over sodium sulfate. After evaporation of the solvent, the residue was dissolved in 100 ml of dry benzene, treated for 15 minutes with borontrifluoride, and then poured into 2 N sodium hydroxide. After acidification with 2 N hydrochloric acid, the reaction mixture was extracted with ether, the extract was evaporated, and the residue was chromatographed on silicic acid, yielding 5.0 gm (= 23.5% of theory) of 3-hydroxy-4-acetyl-6,6-di-propyl-6H-dibenzo-[b,d]-pyran, m.p. 83°-83.5° C.

Workup

  1. customThe starting compound was prepared
  2. temperatureThe resulting mixture was heated for 3 hours
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ether
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. customAfter evaporation of the solvent
  7. dissolutionthe residue was dissolved in 100 ml of dry benzene
  8. additiontreated for 15 minutes with borontrifluoride
  9. additionpoured into 2 N sodium hydroxide
  10. extractionAfter acidification with 2 N hydrochloric acid, the reaction mixture was extracted with ether
  11. customthe extract was evaporated
  12. customthe residue was chromatographed on silicic acid

Sources & evidence

ORD record
ord-5e9bfcde8437493a918f2292032a7083
Source dataset
uspto-grants-1976_10
Patent number
US03987186

Reaction notes

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