Salicylic Acid → HCID 178454881, compound

HRID 921986

Reaction equation

HRID 921986 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[CH2:12]([P+:16]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15]>CC(C)=O>[C:1]([O-:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:25]([P+:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:26][CH2:27][CH3:28].[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Product 1

HCID 178454881HCID 178454881, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Salicylic acid (5-20 mmol) and tetrabutylphosphonium hydroxide (˜40% sol. in H2O) (3.414 g, 5 mmol) were dissolved in 20 ml of acetone stirred for 15 min at room temperature. The solvent was evaporated and the remaining viscous liquid was dried under reduced pressure (0.01 mbar, 50° C.) with stirring for 24 hrs. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=7.74 (dd, J1=7.7 Hz, J2=1.9 Hz, 1H), 7.32 (dt, J1=7.6 Hz, J2=1.8 Hz, 1H), 6.8 (m, 2H), 2.20 (m, 4 H), 1.41 (m, 8 H), 0.9 (t, J=7.1 Hz, 6 H). 31P-NMR (121.5 MHz, d6-DMSO) δ(ppm)=35.1. 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=171.9(s), 163.1(s), 131.1 (d), 129.8(d), 120.6 (s), 115.7 (d), 115.6 (d), 23.3 (d, J=16.4 Hz), 22.6 (d, J=4.8 Hz), 17.3 (d, J=47.3 Hz), 13.2 (s).

Workup

  1. customThe solvent was evaporated
  2. customthe remaining viscous liquid was dried under reduced pressure (0.01 mbar, 50° C.)
  3. stirringwith stirring for 24 hrs

Sources & evidence

ORD record
ord-79fdd7867a444a6eb52723b3abf9171b
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Linked notes

Loading…