2',4'-Dihydroxyacetophenone → 4-[3-(4-Acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]benzonitrile

HRID 1606814Notes

Reaction equation

HRID 1606814 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])=[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:5]=[CH:6][C:7]([O:11][CH2:22][CH:21]([OH:23])[CH2:20][O:24][C:42]2[CH:43]=[CH:44][C:39]([C:38]#[N:45])=[CH:40][CH:41]=2)=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 69902',4'-DihydroxyacetophenoneHCID 66854Benzyltrimethylammonium hydroxideHCID 57313924HCID 57313924, compound

Product 1

HCID 539131114-[3-(4-Acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 2,4-dihydroxyacetophenone (15.2 g), p-cyano-phenylglycidyl ether (17.5 g) and benzyltrimethyl-ammonium hydroxide (10 drops of a 40% solution) in 2-ethoxyethanol (75 ml) was heated under relux for 48 hours. The solvent was then removed under reduced pressure to give a beige solid. This was triturated with a little ether and filtered to give a pale beige powder, (28.6 g). Recrystallization from ethanol yielded 1-(4-acetyl-3-hydroxy-phenoxy)- 2-hydroxy-3-(p-cyanophenoxy) propane as white needles, m.p. 161.5°-163° C.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customto give a beige solid
  3. customThis was triturated with a little ether
  4. filtrationfiltered
  5. customto give a pale beige powder, (28.6 g)
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-6628b9a8d0e84bd39c69eaf13fbfa72b
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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