Sodium Hydroxide → Diethyl [6-(4-carboxyphenoxy)hexyl]phosphonate

HRID 2051754Notes

Reaction equation

HRID 2051754 reaction equation
[OH-].[Na+].[C:3]([C:8]1[CH:28]=[CH:27][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:10][CH:9]=1)([O:5]CC)=[O:4]>C(O)C>[C:3]([C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:27][CH:28]=1)([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5271409Benzoic acid, 4-((6-(diethoxyphosphinyl)hexyl)oxy)-, ethyl ester

Product 1

HCID 5271411Diethyl [6-(4-carboxyphenoxy)hexyl]phosphonateYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution (21 ml) of 1N sodium hydroxide in ethanol was added to a solution of 8.3 g of diethyl [6-(4-carbethoxyphenoxy)hexyl]phosphonate (Example 8) in 20 ml of ethanol. The reaction mixture was stirred at room temperature for two days. The solid fraction was collected, digested with 100 ml of ether, filtered and dried to give 7.0 g of diethyl [6-(4-carboxyphenoxy)hexyl]phosphonate in the form of its sodium salt, m.p. 215°-216° C.

Workup

  1. customThe solid fraction was collected
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-e1086161db3d4d7494d7ca12ff7fbd34
Source dataset
uspto-grants-1980_01
Patent number
US04182759

Reaction notes

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