Triethyl phosphite → HCID 15045704, compound

HRID 2372681Notes

Reaction equation

HRID 2372681 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:10]Cl.[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>C(#N)C>[CH2:14]([O:13][P:12]([CH2:10][C:3]1[CH:4]=[C:5]([CH:6]=[O:7])[CH:8]=[CH:9][C:2]=1[OH:1])(=[O:19])[O:16][CH2:17][CH3:18])[CH3:15]

Participants

4

Reactant 2

HCID 31215Triethyl phosphite2×HCID 7140230Benzaldehyde, 3-(chloromethyl)-4-hydroxy-

Product 1

HCID 15045704HCID 15045704, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.1 mole 4-Hydroxy-3-chloromethylbenzaldehyde was stirred in 75ml acetonitrile and 0.1 mole triethyl phosphite was added dropwise into the stirring suspension. After all the triethyl phosphite had been added, the reaction was refluxed for 4 hours. The reaction was then cooled to room temperature. The reaction solution was then filtered and the acetonitrile was removed on a rotary evaporator leaving behind a solid. This was recrystallized from THF:hexanes in a -20° C. freezer. The product was isolated on a buchner funnel and washed with -20° C. THF. mp 88°-88.5° C.

Workup

  1. temperaturethe reaction was refluxed for 4 hours
  2. filtrationThe reaction solution was then filtered
  3. customthe acetonitrile was removed on a rotary evaporator
  4. customleaving behind a solid
  5. customThis was recrystallized from THF
  6. customin a -20° C.
  7. customThe product was isolated on a buchner funnel
  8. washwashed with -20° C

Sources & evidence

ORD record
ord-8c80297d663b4dcf812dc066fb45752f
Source dataset
uspto-grants-1992_03
Patent number
US05100654

Reaction notes

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