p-Toluenesulfonic acid → HCID 59450529, compound

HRID 1948660Notes

Reaction equation

HRID 1948660 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[C:12]([O:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH:26](O)[CH2:25][CH2:24]2)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-]S([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[C:12]([O:20][C:21]1[CH:22]=[C:23]2[C:27]([CH:26]=[CH:25][CH2:24]2)=[CH:28][CH:29]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 59450539HCID 59450539, compound

Product 1

HCID 59450529HCID 59450529, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

TsOH (850 mg, 9.449 mmol) was added to a stirred mixture of 1-hydroxy-2,3-dihydro-1H-inden-5-yl benzoate (120 g, 472.441 mmol) and MgSO4 (113.4 g, 944.882 mmol) in toluene at rt under nitrogen, and the reaction mixture was stirred at 90-100° C. overnight. The solid was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (PE) to give the title compound. 1H-NMR (400 MHz, CDCl3): δ 8.22-8.24 (m, 2H), 7.62-7.66 (m, 1H), 7.50-7.54 (m, 2H), 7.42 (d, J=8.1 Hz, 1H), 7.34 (d, J=1.2 Hz, 1H), 7.12 (dd, J=8.1 Hz, J=2.0 Hz, 1H), 6.88-6.90 (m, 1H), 6.57-6.59 (m, 1H), 3.44 (s, 2H) ppm.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (PE)

Sources & evidence

ORD record
ord-6e55e09f7072496785f63414bf45b088
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

Loading…