2',4'-Dihydroxyacetophenone → HCID 21544793, compound

HRID 1606811Notes

Reaction equation

HRID 1606811 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11])=[O:3].[C:12]1([O:18][CH2:19][CH:20]2[O:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(OCCO)C>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][CH:20]([OH:22])[CH2:19][O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[OH:11])(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 69902',4'-DihydroxyacetophenoneHCID 31217Phenyl glycidyl etherHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 21544793HCID 21544793, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of resacetophenone (15.2 g), phenylglycidyl ether (15.0 g) and benzyltrimethylammonium hydroxide (5 drops of a 40% solution) in 2-ethoxyethanol (75 ml) was heated under reflux for 2 days. Removal of solvent under reduced pressure yielded a dark, viscous oil, which was allowed to stand for 48 hours, by which time it had crystallized to a solid mass. This was triturated with a mixture of ether and light petroleum (b.p. 40°-60°.), filtered, washed with a little more ether-petroleum and dried. Crystallization from methanol gave 1-(4-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-phenoxypropane as a greyish-white solid, 9.0 g, m.p. 63°-65°.

Workup

  1. temperatureunder reflux for 2 days
  2. customRemoval of solvent under reduced pressure
  3. customyielded a dark, viscous oil, which
  4. customhad crystallized to a solid mass
  5. customThis was triturated with a mixture of ether and light petroleum (b.p. 40°-60°.)
  6. filtrationfiltered
  7. washwashed with a little more ether-petroleum
  8. customdried
  9. customCrystallization from methanol

Sources & evidence

ORD record
ord-7fc1293f4b7c44039130762e2ace948b
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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