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

HRID 1776333Notes

Reaction equation

HRID 1776333 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 666439704-(4-Methyl-4-(trimethylsilyloxy)pent-2-ynoyl)benzonitrile

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-0b48fa3effd848aa9e13dcf0776e22c4
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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