Sodium Hydroxide → HCID 53786866, compound

HRID 1759318Notes

Reaction equation

HRID 1759318 reaction equation
[OH-].[Na+].[P:3]([O-:20])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:21]([O:28][C:29](=[O:32])[CH:30]=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([O:28][C:29](=[O:32])[CH:30]([P:3]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:20])[OH:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 11008258Benzyl glyoxylateHCID 21904359Dibenzylphosphite

Product 1

HCID 53786866HCID 53786866, compoundYield 61%

Conditions

Temperature
20 °C

Procedure

1.5 ml of a saturated methanolic sodium hydroxide solution are allowed to run rapidly into 45.5 g of dibenzyl phosphite and 28.5 g of glyoxylic acid benzyl ester. The reaction which proceeded is exothermic. The mixture is subsequently stirred at 20° C. for some hours. It is chromatographed on silica gel using methylene chloride containing 5% of methanol. The fraction with a Rf of 0.58 is evaporated, 20 ml of diethyl ether are added to the residue (55.2 g) and 45.0 g of dibenzyloxyphosphinylhydroxy-acetic acid benzyl ester are isolated. Melting point 67°-68° C. Yield: 61%.

Workup

  1. customThe reaction which
  2. customIt is chromatographed on silica gel
  3. customThe fraction with a Rf of 0.58 is evaporated
  4. addition20 ml of diethyl ether are added to the residue (55.2 g) and 45.0 g of dibenzyloxyphosphinylhydroxy-acetic acid benzyl ester
  5. customare isolated

Sources & evidence

ORD record
ord-0a8c73f9428348dd839ddafaccd448d3
Source dataset
uspto-grants-1982_07
Patent number
US04340599

Reaction notes

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