Hydrochloric Acid → (4-Oxocyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

HRID 1855027Notes

Reaction equation

HRID 1855027 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C:13]2([CH2:23][O:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH2:18][CH2:17][C:16](OC)([O:19]C)[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][C:13]2([CH2:23][O:24][S:25]([C:28]3[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=3)(=[O:27])=[O:26])[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90408439(4,4-Dimethoxycyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

Product 1

HCID 88538615(4-Oxocyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)Yield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4,4-dimethoxycyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate) (5.4 g, 10.53 mmol) in THF (20 mL) was added 1 N aq HCl (60 mL, 60.0 mmol) and the reaction mixture was refluxed for 3 h. Volatiles were removed in vacuo, and the aqueous layer was extracted with EtOAc (5×10 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes) to afford the title compound (4.3 g, 87% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 7.78 (d, J=8.3 Hz, 4H), 7.39 (d, J=8.0 Hz, 4H), 3.97 (s, 4H), 2.50 (s, 6H), 2.25 (t, J=7.0 Hz, 4H), 1.75 (t, J=7.0 Hz, 4H).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. customVolatiles were removed in vacuo
  3. extractionthe aqueous layer was extracted with EtOAc (5×10 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude oil was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes)

Sources & evidence

ORD record
ord-737705b2c8ac4b5a80fc5d38b92dd3d2
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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