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

HRID 420192Notes

Reaction equation

HRID 420192 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-92514b0a682d41b8b9d5656e3abc1b86
Source dataset
uspto-grants-2012_01
Patent number
US08093424B2

Reaction notes

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