Hydrochloric Acid → HCID 59304081, compound

HRID 544806Notes

Reaction equation

HRID 544806 reaction equation
[OH:1][CH:2]([CH3:15])[CH2:3][C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])=[O:5].CCN(CC)CC.[S:23](Cl)([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24].Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:30][C:29]1[CH:31]=[CH:32][C:26]([S:23]([O:1][CH:2]([CH3:15])[CH2:3][C:4](=[O:5])[CH:6]2[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]2[CH3:14])(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23456997HCID 23456997, compound

Product 1

HCID 59304081HCID 59304081, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone (1.00 g, 92% pure, 4.38 mmol), DMAP (100 mg), and NEt3 (1.0 ml, 7.2 mmol) in CH2Cl2 (20 ml) was added, at 0° C., tosylchloride (2.02 g, 10.56 mmol). The reaction medium was stirred at room temperature for 4 days. Then, the mixture was acidified with concentrated HCl and extracted twice with ether and washed with water, saturated aqueous NaHCO3 and then with saturated aqueous NaCl. Finally, the organic phases were dried over Na2SO4, concentrated at 50-60°/0.03 mbar). 0.76 g of product were thus obtained (yield: 50%).

Workup

  1. extractionextracted twice with ether
  2. washwashed with water, saturated aqueous NaHCO3
  3. dry with materialFinally, the organic phases were dried over Na2SO4
  4. concentrationconcentrated at 50-60°/0.03 mbar)

Sources & evidence

ORD record
ord-f2d9ff5b15cc40b9a9cb882f8559e4d9
Source dataset
uspto-grants-2011_05
Patent number
US07935669B2

Reaction notes

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