Phenol → HCID 2671347, compound

Temperature

0 °C

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 (400 Mz, 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].

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

ORD record

ord-b4a8171ef7c64cb286696a19424a0981

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410119B2