Diethyl Ether → HCID 21544813, compound

HRID 1606813Notes

Reaction equation

HRID 1606813 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].[C:6]([C:9]1[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][C:10]=1[O:11][CH2:12][CH:13]([OH:24])[CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[CH3:23])(=[O:8])[CH3:7].[CH3:30][CH2:31][O:32]CC>C(OCC)(=O)C(OCC)=O.C(O)C.Cl>[C:2]([C:3]1[O:29][C:28]2[C:9]([C:6](=[O:8])[CH:7]=1)=[C:10]([O:11][CH2:12][CH:13]([OH:24])[CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[CH3:23])[CH:25]=[CH:26][CH:27]=2)([O:32][CH2:31][CH3:30])=[O:1]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21544839HCID 21544839, compound

Product 1

HCID 21544813HCID 21544813, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent2×HCID 7268Diethyl OxalateSolvent

Procedure

To a suspension of sodium ethoxide, prepared from sodium (3.0 g) and ethanol (30 ml), in dry ether (200 ml), was added a solution of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-(2,5-dimethylphenoxy) propane (13.2 g) in diethyl oxalate (15 ml). The resultant solution was heated under reflux for 2 hours, and then poured onto ice (100 g). After acidification with a solution of acetic acid (12 ml) in water (80 ml), the ether layer was separated, and the aqueous layer extracted with ether (3 × 25 ml). The combined ethereal extracts were evaporated under reduced pressure to give a yellow oil. This was dissolved in ethanol (96%, 100 ml) containing hydrochloric acid (10 drops) and heated under reflux for 1 hour. Removal of the ethanol under reduced pressure gave 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-(2,5-dimethylphenoxy) propane as a yellow gum (15.2 g) which could not be crystallized.

Workup

  1. temperatureunder reflux for 2 hours
  2. additionpoured onto ice (100 g)
  3. customAfter acidification with a solution of acetic acid (12 ml) in water (80 ml), the ether layer was separated
  4. extractionthe aqueous layer extracted with ether (3 × 25 ml)
  5. customThe combined ethereal extracts were evaporated under reduced pressure
  6. customto give a yellow oil
  7. temperatureheated
  8. temperatureunder reflux for 1 hour
  9. customRemoval of the ethanol under reduced pressure

Sources & evidence

ORD record
ord-f25a4ef86e374c9caa63d5cb18590b1c
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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