4-Toluenesulfonyl chloride → HCID 58421305, compound

HRID 2278970Notes

Reaction equation

HRID 2278970 reaction equation
[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[CH2:4][CH2:5][OH:6].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl>[CH3:19][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])([CH3:8])[CH3:7])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 62118Methoxymethylbutanol

Product 1

HCID 58421305HCID 58421305, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methoxy-3-methylbutan-1-ol (2.50 g, 21.16 mmol) in DCM (30 mL) was treated with p-toluene sulfonyl chloride (5.00 g, 26.2 mmol) followed by TEA (4.28 g, 42.3 mmol) and stirred at RT for 3 h. The mixture was washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate (2.84 g, 49%). 1H NMR (400 MHz, DMSO-d6): δ 7.76 (d, J=8.2 Hz, 2 H), 7.45 (d, J=8.1 Hz, 2 H), 4.03 (t, J=7.2 Hz, 2 H), 2.96 (s, 3 H), 2.38 (s, 3 H), 1.75 (t, J=7.2 Hz, 2 H), 1.01 (s, 6 H); MS (ESI) m/z: 295.0 (M+Na+).

Workup

  1. washThe mixture was washed with satd
  2. dry with materialNaHCO3, then brine, dried over Na2SO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-97a31ba767144abd8add8c7f2c4968fd
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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