10-Undecen-1-ol → (11-Hydroxy-undecyl)-(2,4,4-trimethylpentyl)-phosphinic acid

HRID 1661850

Reaction equation

[CH3:1][CH:2]([CH2:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:3][PH:4](=[O:6])[OH:5].[CH2:12]([OH:23])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22]>C(OOC(CC)(C)C)(CC)(C)C>[OH:23][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][P:4]([CH2:3][CH:2]([CH3:1])[CH2:7][C:8]([CH3:10])([CH3:9])[CH3:11])(=[O:5])[OH:6]

Participants

Conditions

Temperature: 140 °C

Procedure

5 g (0.028 moles) of 2,4,4-trimethylpentyl phosphinic acid, 4.78 g (0.28 moles) of 10-undecen-1-ol and 0.3 mL (0.0014 moles) of di-tert-amylperoxide is mixed in a 50 mL single neck flask. The mixture is purged with argon to remove oxygen and is heated under argon for 5 hours at 140° C. Tert-amyl alcohol is removed by distillation and 9.8 g (quantitative yield) of (11-hydroxy-undecyl)-(2,4,4-trimethylpentyl)-phosphinic acid is obtained as a viscous oil.

Workup

customThe mixture is purged with argon
customto remove oxygen
customTert-amyl alcohol is removed by distillation

Sources & evidence

ORD record: ord-fe181a46ac0145f28fe982b18644a501
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030435B2

Linked notes

Loading…