Phenol → HCID 2671347, compound

HRID 1864166Notes

Reaction equation

HRID 1864166 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(Cl)(=O)C(Cl)=O.[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[C:20]1([O:10][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 77670p-(Methylsulphonyl)benzoic acid

Product 1

HCID 2671347HCID 2671347, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the 4-methanesulfonyl-benzoic acid (20 g, 99.9 mmol) in CH2Cl2 (150 mL), was oxalyl chloride (13.1 mL, 149.9 mmol) added. The reaction mixture was cooled to 0° C. and treated with DMF (2 mL). The reaction was warmed to room temperature and maintained for 10 h. The reaction was concentrated under vacuum and dissolved with CH2Cl2 (200 mL). The reaction was treated with phenol (10.5 mL, 120 mmol) followed by Et3N (16.7 mL, 120 mmol) at 0° C. The reaction was warmed to room temperature and stirred for 7 hr. The reaction was extracted with CH2Cl2 (500 mL), dried and concentrated under vacuum. The desired compound, 4-methanesulfonyl-benzoic acid phenyl ester, was obtained by recrystallization from methanol (200 mL) as a white crystal in 78% yield (21.5 g). 1H NMR (400Mz, DMSO-d6) δ 8.41 (d, J=7.1, 2H), 8.39 (d, J=7.1, 2H), 7.55˜7.51 (m, 2H), 7.37˜7.35 (m, 3H), 3.35 (s, 3H). LCMS 277.0 [M+H].

Workup

  1. additionadded
  2. temperatureThe reaction was warmed to room temperature
  3. temperaturemaintained for 10 h
  4. concentrationThe reaction was concentrated under vacuum
  5. dissolutiondissolved with CH2Cl2 (200 mL)
  6. temperatureThe reaction was warmed to room temperature
  7. extractionThe reaction was extracted with CH2Cl2 (500 mL)
  8. customdried
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-89af754c767446d1bccdcf7517fb910b
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

Loading…