Acetic Acid → HCID 54327688, compound

HRID 1606819Notes

Reaction equation

HRID 1606819 reaction equation
[C:1]([C:4]1[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][C:5]=1[O:6][CH2:7][CH:8]([OH:19])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])(=[O:3])[CH3:2].[O-:25][CH2:26][CH3:27].[Na+].[Na].[C:30](O)(=[O:32])[CH3:31]>C(OCC)(=O)C(OCC)=O.CCOCC.O.C(O)C.Cl>[C:26]([C:27]1[O:24][C:23]2[C:4]([C:1](=[O:3])[CH:2]=1)=[C:5]([O:6][CH2:7][CH:8]([OH:19])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])[CH:20]=[CH:21][CH:22]=2)([O:32][CH2:30][CH3:31])=[O:25]

Participants

10

Reactant 4

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21544809HCID 21544809, compound

Product 1

HCID 54327688HCID 54327688, compound

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 7268Diethyl OxalateSolvent

Procedure

A suspension of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3 -(2,4-dichlorophenoxy) propane (29.6 g) in diethyl oxalate (30 ml) was added to a suspension of sodium ethoxide, prepared from sodium (6.0 g) and ethanol (60 ml) in dry ether (400 ml). The resulting mixture was heated under reflux for 2 hours, cooled, and then poured onto ice (200 g). After acidifying with a solution of acetic acid (24 ml) in water (160 ml) the ethereal layer was separated. The aqueous layer was extracted with ether (3 × 50 ml) and the combined extracts evaporated to give a red oil. This was dissolved in ethanol (96%, 100 ml) containing hydrochloric acid (10 drops) and the solution heated under reflux for 1 hour. The solvent was then removed under reduced pressure to give a red oil which was solidified by triturating with ether. This solid was crystallized from ethanol to yield 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-(2,4-dichlorophenoxy) propane (30.5 g) as cream crystals m.p. 98°-100° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. additionpoured onto ice (200 g)
  5. customwas separated
  6. extractionThe aqueous layer was extracted with ether (3 × 50 ml)
  7. customthe combined extracts evaporated
  8. customto give a red oil
  9. temperaturethe solution heated
  10. temperatureunder reflux for 1 hour
  11. customThe solvent was then removed under reduced pressure
  12. customto give a red oil which
  13. customby triturating with ether
  14. customThis solid was crystallized from ethanol

Sources & evidence

ORD record
ord-e3342f47fb5c4983a9d9683a2e53aeec
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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