Phenolphthalein → HCID 13023269, compound

HRID 1106211Notes

Reaction equation

HRID 1106211 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][C:18]#[C:19][CH2:20][Cl:21])=[O:15].[OH-].[Na+].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1>O>[Cl:21][CH2:20][C:19]#[C:18][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]

Participants

6

Reactant 4

HCID 4764Phenolphthalein2×HCID 14798Sodium Hydroxide2×HCID 13305545HCID 13305545, compoundHCID 131712655HCID 131712655, compound

Product 1

HCID 13023269HCID 13023269, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution containing 21.3 (0.1 mol) of disodium-N-phosphonomethylglycine in water at a temperature of 10°-15° C. was slowly added 17.5 g (0.105 mol) of 4-chloro-2-butynyl chloroformate. A 50% sodium hydroxide solution was slowly added to the reaction mixture to a phenolphthalein endpoint. The addition of the sodium hydroxide solution was repeated until the phenolphthalein endpoint was stable. The resulting mixture was extracted with diethyl ether. The layers were separated and the aqueous layer was acidified with hydrochloric acid, then passed over acid Dowex-50 ion exchange resin. The eluate was concentrated in vacuo yielding a residual gum which was dried over potassium hydroxide pellets (at 1 mm Hg) to yield N-[(4-chloro-2-butynyl)oxy]carbonyl-N-phosphonomethylglycine (11.3 g; 38% yield) as a tan glass having the following analysis: Calculated: Cl, 11.83; P, 10.34. Found: Cl, 12.82; P, 11.03.

Workup

  1. extractionThe resulting mixture was extracted with diethyl ether
  2. customThe layers were separated
  3. concentrationThe eluate was concentrated in vacuo
  4. customyielding a residual gum which
  5. dry with materialwas dried over potassium hydroxide pellets (at 1 mm Hg)

Sources & evidence

ORD record
ord-986adf8144f648a3b16c01308216afd2
Source dataset
uspto-grants-1982_01
Patent number
US04312662

Reaction notes

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