Methanol → (3-hydroxy-butyl)-phenyl Dodecylphosphinic Acid

HRID 2087096Notes

Reaction equation

HRID 2087096 reaction equation
[C:1]1(P(=O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][CH:11]([OH:14])[CH:12]=[CH2:13].CO.[CH2:17](B(CC)CC)[CH3:18].O[CH:25]([CH3:37])[CH2:26][CH2:27][P:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])[OH:29]>>[OH:14][CH:11]([CH3:10])[CH2:12][CH2:13][O:29][P:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH2:27][CH2:26][CH2:25][CH2:37][CH2:17][CH2:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:1])=[O:30]

Participants

6

Reactant 5

HCID 887MethanolHCID 7357TriethylboraneHCID 117163-Buten-2-olHCID 12009734(3-Hydroxy-butyl) phenylphosphinic acidHCID 178527038HCID 178527038, compound

Product 1

HCID 69890855(3-hydroxy-butyl)-phenyl Dodecylphosphinic Acid

Procedure

The procedure as for Example 5 was repeated using 1.08 g (7.6 mmol) of phenylphosphinic acid, 0.45 g (6.2 mmol) of but-3-en-2-ol and at a temperature of minus 15° C. The reactants were added to 5 g (156 mmol) of methanol. 0.8 ml (0.8 mmol) of molar triethylborane was slowly added to the mix. The yield of product obtained was 84% and was identified by 1H and 31P NMR as (3-hydroxy-butyl) phenylphosphinic acid.

Workup

  1. custom15° C
  2. customThe yield of product obtained

Sources & evidence

ORD record
ord-167c58b88a704fea88c32b4f0a33c40c
Source dataset
uspto-grants-2004_04
Patent number
US06727378B2

Reaction notes

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