Phenolphthalein → HCID 13023279, compound

HRID 1106212Notes

Reaction equation

HRID 1106212 reaction equation
[Na][Na].[P:3]([CH2:7][NH:8][CH2:9][C:10]([OH:12])=[O:11])([OH:6])([OH:5])=[O:4].Cl[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15].[OH-].[Na+].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1>O>[CH2:17]([O:16][C:14]([N:8]([CH2:7][P:3]([OH:6])([OH:5])=[O:4])[CH2:9][C:10]([OH:12])=[O:11])=[O:15])[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 4764PhenolphthaleinHCID 14798Sodium HydroxideHCID 61140Butyl chloroformateHCID 131712655HCID 131712655, compound

Product 1

HCID 13023279HCID 13023279, compoundYield 157.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution containing 16.9 g (0.10 mol) of disodium-N-phosphonomethylglycine in water at 20°-25° C. was added 15 g (0.11 mol) of n-butyl chloroformate. After stirring the reaction mixture for 2 hours, a 50% sodium hydroxide solution was slowly added until the pH of the mixture stabilized at a phenolphthalein endpoint. The reaction mixture was concentrated and the residue dried over potassium hydroxide pellets to yield 42.3 g of N-n-butoxycarbonyl-N-phosphonomethylglycine, disodium salt, as a white solid having the following analysis: Calculated: C, 33.00; H, 5.19; P, 10.64. Found: C, 32.77; H, 5.16; P, 10.69.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dry with materialthe residue dried over potassium hydroxide pellets

Sources & evidence

ORD record
ord-ba04bb78cb9948f4a5bd4558fe5ea309
Source dataset
uspto-grants-1982_01
Patent number
US04312662

Reaction notes

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