4-Toluenesulfonyl chloride → 2-(4-Formylphenoxy)ethyl 4-methylbenzenesulfonate

HRID 2362816Notes

Reaction equation

HRID 2362816 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[OH:19][CH2:20][CH2:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:19][CH2:20][CH2:21][O:22][C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-HCID 516892Sodium Bicarbonate

Product 1

HCID 37755262-(4-Formylphenoxy)ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At RT, 12.6 ml (90.3 mmol) of triethylamine and a solution of 13.77 g (72.2 mmol) of toluene-4-sulphonyl chloride in 200 ml of dichloromethane are successively added dropwise with stirring to a solution of 10.0 g (60.2 mmol) of 4-(2-hydroxyethoxy)benzaldehyde in 300 ml of dichloromethane. The reaction mixture is stirred at RT for 12 h. After addition of 0.15 g (1.2 mmol) of 4-N,N-dimethylaminopyridine, the mixture is stirred at RT for another 4 h. 250 ml of saturated aqueous sodium bicarbonate solution are then added, and the mixture is extracted three times with in each case 100 ml of dichloromethane. The combined organic phases are dried over sodium sulphate. After removal of the solvent on a rotary evaporator, the crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane→ethyl acetate).

Workup

  1. stirringthe mixture is stirred at RT for another 4 h
  2. extractionthe mixture is extracted three times with in each case 100 ml of dichloromethane
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customAfter removal of the solvent
  5. customon a rotary evaporator
  6. customthe crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane→ethyl acetate)

Sources & evidence

ORD record
ord-b380014bcb4b4b32b020e2a165c54a41
Source dataset
uspto-grants-2014_04
Patent number
US08691850B2

Reaction notes

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