Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 18332478, compound

HRID 2268757Notes

Reaction equation

HRID 2268757 reaction equation
C(OC([O:6][CH2:7][C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH:10]([C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)[O:11][CH3:12])C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Cl-].[Na+].O>[OH:6][CH2:7][C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH:10]([C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)[O:11][CH3:12]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 18332474HCID 18332474, compound

Product 1

HCID 18332478HCID 18332478, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To 3.05 g (10 mmol) of 5-[2-(1-ethoxyethyl)oxymethyl-α-methoxybenzyl]-3-methylisoxazole was added 0.25 g (1 mmol) of pyridinium p-toluenesulfonate and stirred under reflux for an hour. After completion of the reaction, 150 ml of brine was added and extracted twice with 80 ml of dichloromethane. The extract was dried over anhydrous magnesium and concentrated under reduced pressure to give 5-(2-hydroxymethyl-α-methoxybenzyl)-3-methylisoxazole (2.33 g, 99.9%) as colorless oil.

Workup

  1. temperatureunder reflux for an hour
  2. additionwas added
  3. extractionextracted twice with 80 ml of dichloromethane
  4. dry with materialThe extract was dried over anhydrous magnesium
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-762c05adcdb849368f83b49e0abbe746
Source dataset
uspto-grants-2001_12
Patent number
US06329371B1

Reaction notes

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