p-Toluenesulfonic acid → 4-(4-Hydroxy-4-methylpent-2-ynoyl)benzonitrile

HRID 655427Notes

Reaction equation

HRID 655427 reaction equation
[CH3:1][C:2]([O:16][Si](C)(C)C)([CH3:15])[C:3]#[C:4][C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6].CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[OH:16][C:2]([CH3:15])([CH3:1])[C:3]#[C:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([C:11]#[N:12])=[CH:13][CH:14]=1)=[O:6]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66643970HCID 66643970, compound

Product 1

HCID 666439664-(4-Hydroxy-4-methylpent-2-ynoyl)benzonitrileYield 112.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4-methyl-4-(trimethylsilyloxy)pent-2-ynoyl)benzonitrile (1.7 g, 5.00 mmol) in DCM (15 mL) was added PTSA (1.70 g, 8.90 mmol) at RT and the reaction mixture was stirred for 30 min. The reaction mixture was diluted with water (10 mL) and extracted with DCM (2×50 mL). The combined organic layers were washed with a saturated NaHCO3 solution and water, dried over Na2SO4, filtered, and then concentrated in vacuo to afford 4-(4-hydroxy-4-methylpent-2-ynoyl)benzonitrile (1.20 g) as a yellow oil.

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washThe combined organic layers were washed with a saturated NaHCO3 solution and water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36ee0d190e194b09a681c48a687e0801
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

Loading…