Salicylic Acid → HCID 178421851, compound

HRID 921991Notes

Reaction equation

HRID 921991 reaction equation
[C:1]12([CH2:11][S:12]([OH:15])(=[O:14])=[O:13])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[C:16]([OH:25])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].[OH-].[CH2:27]([P+:31]([CH2:40][CH2:41][CH2:42][CH3:43])([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]>CC(C)=O>[C:16]([O-:25])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].[CH2:40]([P+:31]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:36][CH2:37][CH2:38][CH3:39])[CH2:41][CH2:42][CH3:43].[C:1]12([CH2:11][S:12]([OH:15])(=[O:13])=[O:14])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Product 1

HCID 178421851HCID 178421851, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Camphorsulphonic acid (5 mmol), salicylic acid (0.6909 g, 5 mmol) and tetrabutylphosphonium hydroxide (˜40% sol. in H2O) (3.414 g, 5 mmol) were dissolved in 20 ml of acetone and stirred for 15 min at room temperature. The solvent was evaporated and the remaining viscous liquid was dried at 0.01 mbar with stirring for 24 hrs. The desired compound is isolated as a colourless liquid; 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=7.79 (dd, J1=7.9 Hz, J2=1.8 Hz), 7.52 (m, 1H), 6.94 (m, 3H), 2.97 (d, J=14.8 Hz, 1H), 2.71 (quin, J=10.8 Hz, 1H), 2.36 (d, J=14.8 Hz, 1H), 2.19 (m, 9H), 1.93 (t, J=4.5 Hz, 1H), 1.84 (m, 2H), 1.42 (m, 16 H), 1.26 (m, 2H), 1.05 (s, 3H), 0.91 (t, J=6.9 Hz, 12H), 0.74 (s, 3H). Tg−33° C., T5% onset 203° C.

Workup

  1. customThe solvent was evaporated
  2. customthe remaining viscous liquid was dried at 0.01 mbar
  3. stirringwith stirring for 24 hrs

Sources & evidence

ORD record
ord-1bde020c738d42c4b21995a3b4aab939
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Reaction notes

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