Water → 2-Naphthyl p-Toluenesulfonate

HRID 590003Notes

Reaction equation

HRID 590003 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.O>C1(C)C=CC=CC=1>[S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)([O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86632-Naphthol

Product 1

HCID 2218592-Naphthyl p-ToluenesulfonateYield 87.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 2 L four-necked round-bottomed flask equipped with a Teflon® coated magnetic stirring bar, dropping funnel, thermometer, and a gas inlet was evacuated and filled with nitrogen. 2-naphthol (51.8 g, 359.3 mmol, 1.0 equivalent), dehydrated toluene (800 mL), and triethylamine (52.6 mL, 377.3 mmol, 1.05 equivalents) were charged into the flask successively. Subsequently, to the solution was added p-toluenesulfonyl chloride (69.9 g, 366.5 mmol, 1.02 equivalents) in dehydrated toluene (140 mL) dropwise via the dropping funnel over 15 minutes at such a rate that the internal temperature was kept at 50° C. or lower, and the mixture was stirred for further 2 hours at room temperature. The thus-obtained white suspension was poured into water, and the aqueous layer was separated off. The organic layer was passed through a silica gel pad, and concentrated under reduced pressure to give solid residue, which was purified by recrystallization from toluene/methanol to afford 94.2 g of 2-naphthyl tosylate as a white powder. The mother liquor was concentrated under reduced pressure to give solid residue, which was recrystallized to recover further 9.2 g of 2-naphthyl tosylate.

Workup

  1. customthermometer, and a gas inlet was evacuated
  2. additionfilled with nitrogen
  3. customwas kept at 50° C.
  4. customthe aqueous layer was separated off
  5. concentrationconcentrated under reduced pressure
  6. customto give solid residue, which
  7. customwas purified by recrystallization from toluene/methanol

Sources & evidence

ORD record
ord-f2abf2b9402b47a793358022bb91b87f
Source dataset
uspto-grants-2016_01
Patent number
US09233922B2

Reaction notes

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