p-Toluenesulfonic acid → HCID 59354750, compound

HRID 1258302Notes

Reaction equation

HRID 1258302 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[C:9]#[C:10][C:11]([CH3:18])([O:13][Si](C)(C)C)[CH3:12])=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:19])[C:9]#[C:10][C:11]([OH:13])([CH3:12])[CH3:18])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59354751HCID 59354751, compound

Product 1

HCID 59354750HCID 59354750, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(4-chlorophenyl)-4-methyl-4-(trimethylsilyloxy)pent-2-yn-1-one (3.7 g, 12.50 mmol) in DCM (20 mL) was added PTSA (2.87 g, 15.01 mmol) at RT. The reaction mixture was stirred for 1 h and diluted with water (10 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 1-(4-chlorophenyl)-4-hydroxy-4-methylpent-2-yn-1-one (2.40 g) as a pale red oil.

Workup

  1. washThe combined organic layers were washed with a saturated NaHCO3 solution and water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b117a41915c443c6a5490b903588b66d
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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