Ethanol → HCID 21544808, compound

HRID 1606804Notes

Reaction equation

HRID 1606804 reaction equation
[C:1]([C:4]1[C:25]([OH:26])=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][CH2:7][CH:8]([OH:21])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[O-:27][CH2:28][CH3:29].[Na+].[Na].C([OH:34])C>C(OCC)(=O)C(OCC)=O.CCOCC>[C:28]([C:29]1[O:26][C:25]2[C:4]([C:1](=[O:3])[CH:2]=1)=[C:5]([O:6][CH2:7][CH:8]([OH:21])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:18])([CH3:19])[CH3:20])=[CH:13][CH:12]=1)[CH:22]=[CH:23][CH:24]=2)([OH:34])=[O:27]

Participants

7

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 53955912HCID 53955912, compound

Product 1

HCID 21544808HCID 21544808, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7268Diethyl OxalateSolvent

Procedure

A solution of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-p-t-butylphenoxypropane (14.4 g) in diethyl oxalate (15 ml) was added to a suspension of sodium ethoxide, prepared from sodium (3.0 g) and ethanol (30 ml), in ether (200 ml). The mixture was heated under reflux for 1.5 hours, and the brown-coloured residue was 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 solution extracted with ether (3 × 25 ml). The solvent was then removed from the combined ethereal layer and ethereal extracts. The residue was dissolved in a mixture of acetic acid (80 ml) and hydrochloric acid (30 ml) and heated under reflux for 1 hour. On pouring into water (1 L) 1-(2-carboxychromon-5-yloxy)-3-p-t-butylphenoxypropane, 10.7 g, was obtained as a beige gum.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. additionthe brown-coloured residue was poured onto ice (100 g)
  4. customAfter acidification with a solution of acetic acid (12 ml) in water (80 ml), the ether layer was separated
  5. extractionthe aqueous solution extracted with ether (3 × 25 ml)
  6. customThe solvent was then removed from the combined ethereal layer and ethereal extracts
  7. dissolutionThe residue was dissolved in a mixture of acetic acid (80 ml) and hydrochloric acid (30 ml)
  8. temperatureheated
  9. temperatureunder reflux for 1 hour
  10. additionOn pouring into water (1 L) 1-(2-carboxychromon-5-yloxy)-3-p-t-butylphenoxypropane, 10.7 g
  11. customwas obtained as a beige gum

Sources & evidence

ORD record
ord-dc4926a4f35647dc9b57de3780401853
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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