4-Toluenesulfonyl chloride → 1,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate

HRID 1719820Notes

Reaction equation

HRID 1719820 reaction equation
[CH3:1][O:2][C:3]([O:19][CH3:20])([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)[CH:4]([OH:6])[CH3:5].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:6][CH:4]([CH3:5])[C:3]([O:19][CH3:20])([O:2][CH3:1])[C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=3)[CH:8]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chloride2×HCID 113003471,1-Dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol

Product 1

HCID 200291641,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

The oil, 1,1-dimethoxy-1-(6-methoxy-2-naphthyl) propan-2-ol, prepared in Example 29 is dissolved in 60 ml of pyridine and cooled to 10° C. Then 13 g of p-toluenesulfonyl chloride is added and the reaction mixture is stirred to dissolve the p-toluenesulfonyl chloride. The reaction mixture is allowed to stand overnight and the precipitation of pyridine hydrochloride is observed. The reaction mixture is poured into 7 volumes of water and extracted with ethyl ether. The ethereal layer is washed with dilute hydrochloric acid and then with dilute sodium hydroxide. The ethereal extract is dried over magnesium sulfate and evaporated to yield 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate, as an oil, [which is characterized by an NMR spectra in duterochloroform of τ=8.86 (doublet, J=2.5), 7.57, 6.82, 6.74, 6.09, 4.87 (quartet, J=2.5), 2.2-3.0 (multiplet)].

Workup

  1. customthe precipitation of pyridine hydrochloride
  2. additionThe reaction mixture is poured into 7 volumes of water
  3. extractionextracted with ethyl ether
  4. washThe ethereal layer is washed with dilute hydrochloric acid
  5. extractionThe ethereal extract
  6. dry with materialis dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-82e9803cbf6e423ca4bdc6b425c958c9
Source dataset
uspto-grants-1985_09
Patent number
US04542237

Reaction notes

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