4-Toluenesulfonyl chloride → (4,4-Dimethoxycyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

HRID 1855026Notes

Reaction equation

HRID 1855026 reaction equation
[CH3:1][O:2][C:3]1([O:13][CH3:14])[CH2:8][CH2:7][C:6]([CH2:11][OH:12])([CH2:9][OH:10])[CH2:5][CH2:4]1.[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>N1C=CC=CC=1.CCOC(C)=O>[CH3:22][C:21]1[CH:23]=[CH:24][C:18]([S:15]([O:12][CH2:11][C:6]2([CH2:9][O:10][S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:5][CH2:4][C:3]([O:2][CH3:1])([O:13][CH3:14])[CH2:8][CH2:7]2)(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 90408533[1-(Hydroxymethyl)-4,4-dimethoxycyclohexyl]methanol

Product 1

HCID 90408439(4,4-Dimethoxycyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)Yield 60%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4,4-dimethoxycyclohexane-1,1-diyl)dimethanol (3.6 g, 17.62 mmol) in pyridine (20 mL) was added tosyl chloride (7.39 mL, 38.8 mmol). The reaction mixture was stirred at rt for 18 h and then diluted with EtOAc (50 mL). The organic mixture and washed with 10% aq. citric acid, dried (Na2SO4) and concentrated in vacuo to afford the title compound (5.4 g, 60% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.73 (d, J=8.3 Hz, 4H), 7.35 (d, J=8.2 Hz, 4H), 3.84 (s, 4H), 3.09 (s, 6H), 2.45 (s, 6H), 1.54-1.45 (m, 4H), 1.42-1.34 (m, 4H).

Workup

  1. washThe organic mixture and washed with 10% aq. citric acid
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-380a28ef96824bb6bbebc81431eed06b
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

Loading…