Lactic Acid → HCID 86662333, compound

HRID 921990

Reaction equation

HRID 921990 reaction equation
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[OH-].[CH2:8]([P+:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:10][CH3:11]>CC(C)=O>[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[CH2:21]([P+:12]([CH2:8][CH2:9][CH2:10][CH3:11])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23][CH3:24].[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3]

Participants

4

Reactant 2

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

Product 1

HCID 86662333HCID 86662333, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Lactic acid (5-15 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 0.1 mbar with stirring for 24 hrs. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=3.84 (br s, 1H), 3.44 (q, J=6.7 Hz, 1H), 2.18 (m, 8H), 1.41 (m, 16H), 1.05 (d, J=7.2 Hz, 3H), 0.91 (t, J=6.7 Hz, 12H). 31P-NMR (121.5 MHz, d6-DMSO) δ(ppm)=35.0. 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=176.8, 67.3, 23.72 (d, J=15.5 Hz), 23.01 (d, J=4.7 Hz), 21.91, 17.70 (d, J=47.9 Hz), 13.62 (s).

Workup

  1. customThe solvent was evaporated
  2. customthe remaining viscous liquid was dried at 0.1 mbar
  3. stirringwith stirring for 24 hrs

Sources & evidence

ORD record
ord-e9c6d42dd0644bca9bd18c739c33c49e
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Linked notes

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