Water → Toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl ester

HRID 38364

Reaction equation

HRID 38364 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[OH:12])([CH3:3])[CH3:2].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>C(Cl)Cl>[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[O:12][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 183649974-Methoxy-2-(propan-2-yl)phenol

Product 1

HCID 44248852Toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl esterYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-isopropyl-4-methoxy-phenol (56.91 g, 342 mmol) triethylamine (57.3.0 ml, 411 mmol) in 750 ml CH2Cl2 was cooled to 0° C. p-Toluenesulfonyl chloride (68.54 g, 360 mmol) in 250 ml CH2Cl2 was added drop-wise at a rate that maintained the internal temperature <10° C. The mixture was allowed to warm to rt. After 16 h, H2O was added and the mixture was extracted with CH2Cl2. The combined organics were washed with brine, dried with Na2SO4, filtered and concentrated in vacuo to afford a crude solid. Recrystallization from hexanes afforded toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl ester (81.67 g, 74%) as white needles.

Workup

  1. additionwas added drop-wise at a rate that
  2. temperaturemaintained the internal temperature <10° C
  3. extractionthe mixture was extracted with CH2Cl2
  4. washThe combined organics were washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a crude solid
  9. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-0714b4c1df794bfe8572118df2c895e7
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Linked notes

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