2-Acetylhydroquinone → HCID 54175761, compound

HRID 1606816Notes

Reaction equation

HRID 1606816 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].C(C1C=CC([CH:20]([O:24]C(C2C=CC(C#N)=CC=2)C2OC2)[CH:21]2[O:23][CH2:22]2)=CC=1)#N.[OH-].[CH2:38]([N+:45](C)(C)C)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(OCCO)C>[C:2]([C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[OH:11])[O:10][CH2:22][CH:21]([OH:23])[CH2:20][O:24][C:42]1[CH:43]=[CH:44][C:39]([C:38]#[N:45])=[CH:40][CH:41]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 102792-AcetylhydroquinoneHCID 66854Benzyltrimethylammonium hydroxideHCID 57313924HCID 57313924, compound

Product 1

HCID 54175761HCID 54175761, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 2,5 -dihydroxyacetophenone (30.4 g), p-cyanophenylglycidyl ether (35.0 g) and benzyltrimethylammonium hydroxide (10 drops of a 40% solution) in 2-ethoxyethanol (150 ml) was heated under reflux for 72 hours. The solvent was then removed under reduced pressure to give a dark viscous oil which rapidly solidified. This solid was extracted with ether in a Soxhlet thimble and the ether then removed to give a yellow solid residue. This was triturated with a little ethanol, filtered off, washed with a little more ethanol and dried. Some further material was obtained by grinding the residue from the Soxhlet thimble and extracting it with boiling ether. Recrystallization from aqueous ethanol gave 1-(3-acetyl-4-hydroxyphenoxy)-2 -hydroxy-3-(p-cyano-phenoxy) propane as lemon-yellow needles m.p. 118°-120° C.

Workup

  1. temperatureunder reflux for 72 hours
  2. customThe solvent was then removed under reduced pressure
  3. customto give a dark viscous oil which
  4. extractionThis solid was extracted with ether in a Soxhlet thimble
  5. customthe ether then removed
  6. customto give a yellow solid residue
  7. customThis was triturated with a little ethanol
  8. filtrationfiltered off
  9. washwashed with a little more ethanol
  10. customdried
  11. customSome further material was obtained
  12. customby grinding the residue from the Soxhlet thimble
  13. extractionextracting it with boiling ether
  14. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-570d568282f0424281f939a066f77c0b
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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