Salicylic Acid → HCID 178473643, compound

HRID 921992

Reaction equation

HRID 921992 reaction equation
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:7]([OH:16])(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].[OH-].[CH2:18]([P+:22]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>CC(C)=O>[C:7]([O-:16])(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].[CH2:31]([P+:22]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:32][CH2:33][CH3:34].[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 612Lactic AcidHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Product 1

HCID 178473643HCID 178473643, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Lactic acid (0.4504 g, 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)=7.63 (dd, J1=7.6 Hz, J2=1.9 Hz), 7.11 (m, 1H), 6.58 (m, 3H), 4.03 (q, J=6.9 Hz, 1H), 2.17 (m, 8H), 1.42 (m, 16 H), 1.23 (d, 7.0 Hz, 3H), 0.90 (t, J=7.3 Hz, 12 H). 31P-NMR (121.5 MHz, d6-DMSO) δ(ppm)=35.0. 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=176.3, 171.1, 163.0, 131.2, 129.9, 120.5, 117.8, 115.767.3, 23.4 (d, J=15.8 Hz), 22.6 (d, J=4.3 Hz), 20.5, 17.3 (d, J=47.7 Hz), 13.3 (s).

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-0260974b33fc4dec97a88a0eb2af9a0b
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Linked notes

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