Acetic Acid → HCID 15105835, compound

HRID 1087655Notes

Reaction equation

HRID 1087655 reaction equation
[CH:1]1([C:7]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[CH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17](O)(=[O:19])[CH3:18].C(N)(=S)C.CC[O:27]CC>>[C:17]([O:16][C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8](=[O:27])[CH3:9])(=[O:19])[CH3:18]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 2319401-cyclohexyl-1-phenylprop-2-yn-1-olHCID 2723949Thioacetamide

Product 1

HCID 15105835HCID 15105835, compoundYield 66.9%

Procedure

3-Cyclohexyl-3-hydroxy-3-phenylprop-1-yne (21.57 g, 0.10 mol) was added to 100 ml of glacial acetic acid. While the solution was stirred vigorously mercuric acetate (35.20 g, 0.11 mol) was added. The solution was stirred at room temperature for 72 hours and then thioacetamide (8.3 g, 0.11 mol) was added. The solution was stirred an additional 3 hours and 300 ml of ether was added. The reaction mixture was transferred to a separatory funnel and washed with water, saturated sodium bicarbonate solution, and again with water. The ether layer was dried over sodium sulfate and the ether removed under vacuum to afford the product as a white crystalline solid (18.36 g, 66.9%). Mp 81°-83° C. (from petroleum ether). 1H NMR (CDCl3) δ7.3(bs, 5H), 2.2(s, 3H), 1.9(s, 3H), 2.0-0.8(m, 11H).

Workup

  1. additionwas added
  2. stirringThe solution was stirred an additional 3 hours
  3. customThe reaction mixture was transferred to a separatory funnel
  4. washwashed with water, saturated sodium bicarbonate solution
  5. dry with materialThe ether layer was dried over sodium sulfate
  6. customthe ether removed under vacuum

Sources & evidence

ORD record
ord-ddf6bfbbd49d49eebd18cd6556743e1e
Source dataset
uspto-grants-1991_07
Patent number
US05036107

Reaction notes

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