p-Toluenesulfonic acid → HCID 23567163, compound

HRID 1369000Notes

Reaction equation

HRID 1369000 reaction equation
O[C:2]1([C:14]([O:16][CH3:17])=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOCC>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4][CH:3]=[C:2]2[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 79248540HCID 79248540, compound

Product 1

HCID 23567163HCID 23567163, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-hydroxy-7-methoxytetralin-1-yl-carboxylic acid, methyl ester (0.5 g; 2.1 mmol; see Example 1(i) above) in toluene (5 mL) was added to a refluxing solution of p-TsOH (0.6 g; 3.2 mmol) in toluene (10 mL), and the resultant mixture was refluxed for 45 minutes. After cooling, the reaction mixture was diluted with ether, washed with water and NaHCO3/aq, dried with Na2SO4 and concentrated. Yield 392 mg (85%).

Workup

  1. temperatureAfter cooling
  2. washwashed with water and NaHCO3/aq
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d7378c27e03646d8b7ecd401bd2e13ff
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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