p-Toluenesulfonic acid → (6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-ylidene)-acetic acid methyl ester

HRID 971286Notes

Reaction equation

HRID 971286 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1(O)[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[CH:4]=[C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 66651224(6-Benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester

Product 1

HCID 66650886(6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-ylidene)-acetic acid methyl esterYield 81.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of (6-benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester (1.28 g, 3.42 mmol) and para-toluenesulfonic acid (0.50 g) in 250 mL of benzene was refluxed for 2 hours using a Dean-Stark trap. The reaction mixture was cooled and poured into 500 mL of EtOAc, and this organic phase was washed with water, saturated NaHCO3, and dried (MgSO4). Evaporation under reduced pressure gave a dark oil that was purified by elution on silica gel (hexanes:EtOAc 7:3) to yield 0.991 g (2.78 mmol, 81.2% of a white crystalline solid. MS: 357 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washthis organic phase was washed with water, saturated NaHCO3
  3. dry with materialdried (MgSO4)
  4. customEvaporation under reduced pressure
  5. customgave a dark oil that
  6. customwas purified by elution on silica gel (hexanes:EtOAc 7:3)

Sources & evidence

ORD record
ord-3c4f44d0e3da4c519d689d468b8cd8c9
Source dataset
uspto-grants-2007_12
Patent number
US07312359B2

Reaction notes

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