Water → HCID 86761974, compound

HRID 1886750Notes

Reaction equation

HRID 1886750 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][C:14]([OH:17])([CH3:16])[CH3:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([O:17][C:14]([CH3:15])([CH2:13][CH2:12][O:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH3:16])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

Product 1

HCID 86761974HCID 86761974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a mixture of the alcohol 2 (0.500 g, 1.937 mmol), ZrOCl28.H2O (0.0031 g, 0.5 mol %) in methylene chloride (5 mL), acetyl chloride (0.304 g, 3.87 mmol) is added and the reaction is stirred for overnight at 20° C. The reaction on completion, is diluted with methylene chloride (5 mL) and washed with saturated sodium bicarbonate (2×10 mL), brine (1×10 mL) and dried. The solvent is evaporated to get the crude product. 1H NMR (400 MHz, CDCl3): δ 1.54 (s, 6H), 1.59 (s, 3H), 2.14-2.07 (m, 2H), 2.43 (s, 3H), 4.26 (dt, J=6.9, 13.5, 3H), 7.33 (d, J=7.9, 2H), 7.77 (d, J=8.2, 2H).

Workup

  1. customThe reaction on completion
  2. washwashed with saturated sodium bicarbonate (2×10 mL), brine (1×10 mL)
  3. customdried
  4. customThe solvent is evaporated

Sources & evidence

ORD record
ord-3287ab455dec4ad28f192a0ca8432c13
Source dataset
uspto-grants-2013_08
Patent number
US08501382B1

Reaction notes

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