Sulfuric Acid → HCID 11701181, compound

HRID 1389554Notes

Reaction equation

HRID 1389554 reaction equation
[O:1]1CCCC1.S(=O)(=O)(O)O.[OH:11][C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH:15]([CH3:17])[CH3:16])[C:13]#[CH:14]>O>[OH:11][C:12]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH:15]([CH3:17])[CH3:16])[C:13](=[O:1])[CH3:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 582807HCID 582807, compound

Product 1

HCID 11701181HCID 11701181, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a refluxing mixture of tetrahydrofuran (70 ml), water (5 ml), and conc. sulfuric acid (1.5 g) is added 1 g of red mercuric oxide and the reflux is continued for 5 min. Then, the inside temperature is adjusted to 60°-62° C. and 10 g of 3-hydroxy-4-methyl-3-phenyl-1-pentyne (described in Example 1) is added. The reaction is exothermic (spontaneous mild reflux) and there is a noticeable clearing of the mixture. Another 1 g of mercuric oxide is added, and the solution is refluxed for 30 min. The reaction mixture is stirred at 60° C. for an additional 3 hr, during which time the precipitation of a mercury sludge occurred. After cooling, the slurry is diluted with 100 ml of diethyl ether and filtered through diatomaceous earth. The filter cake is washed with 200 ml of diethyl ether, and the combined filtrates are washed repeatedly with water, dried over magneisum sulfate, filtered, and evaporated to give 10.6 g of the title product, ir (CDCl3) 3470 and 1715-1710 cm-1 and nmr (CDCl3) δ 0.91(d), 2.15(s), 2.79(heptuplet), 4.39(s) and 7.20-7.65(m).

Workup

  1. customis adjusted to 60°-62° C.
  2. temperature(spontaneous mild reflux) and there
  3. temperaturethe solution is refluxed for 30 min
  4. customthe precipitation of a mercury sludge
  5. temperatureAfter cooling
  6. additionthe slurry is diluted with 100 ml of diethyl ether
  7. filtrationfiltered through diatomaceous earth
  8. washThe filter cake is washed with 200 ml of diethyl ether
  9. washthe combined filtrates are washed repeatedly with water
  10. dry with materialdried over magneisum sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-6dbee0f179fd477684cdb56873d4bb0c
Source dataset
uspto-grants-1981_01
Patent number
US04244958

Reaction notes

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