4-Toluenesulfonyl chloride → p-Toluenesulfonic acid

HRID 724466Notes

Reaction equation

HRID 724466 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(C1C=CC=C(CC=C)C=1[OH:24])C=C.C1(O)C=CC=CC=1.C(N(CC)CC)C>C(N(CC)CC)C>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:24])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 728562,6-Di(prop-2-en-1-yl)phenolHCID 69595409Phenol--N,N-diethylethanamine (1/1)

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Triethylamine (4 ml) and 4-toluenesulfonyl chloride (3.80 gm, 0.02 mol) were diluted with 1,2-dichloromethane (50 ml) and 2,6-diallylphenol (3.48 gm, 0.02 mol), dissolved in 1,2-dichloromethane (10 ml), was added drop wise to the phenol-triethylamine solution at room temperature and then refluxed for 1 hr. The reaction mixture was cooled, washed with water and dried over MgSO4, filtered and evaporated to give 4-toluenesulfonic acid: 2,6-diallylphenyl ester as an oil. Purification was carried out via filtering a hexane solution of the ester through silica gel. MS m/z 328 (M+ calcd for C19H20O3S=328). H NMR (300 MHz, CDCl3) d 2.50 (s, 3, CH3), 3.25–3.35 (d, 4, CH2), 4.95–5.10 (m, 4, CH2 vinyl), 5.75–5.90 (m, 2, CH, vinyl), 7.10–7.25 (m, 3, aromatic), 7.85–7.95 (m, 2, aromatic). Oxidation of product as described in Example 1 gave 4-toluenesulfonic acid 2,6-di(2,3-epoxypropyl)phenyl ester. MS m/z 360 (M+ calcd for C19H20O5S=360. H NMR (300 MHz, CDCl3) d 2.45–2.55 (m, 2, CH2 epoxypropyl), 2.50 (s, 3, CH3), 2.35–2.95 (m, 6, CH2 epoxypropyl), 3.21–3.35 (m, 2, CH epoxypropyl), 7.25–7.45 (m, 5, aromatic), 7.85–7.95 (d, 2, aromatic).

Workup

  1. temperaturerefluxed for 1 hr
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-92fa32f264d34ac4bbec8b0cbc5510bd
Source dataset
uspto-grants-2006_11
Patent number
US07141684B2

Reaction notes

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