Hydrochloric Acid → HCID 20304544, compound

HRID 236970Notes

Reaction equation

HRID 236970 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[C:6]([CH2:14][OH:15])[C:5]=1[OH:16])(=[O:3])[CH3:2].[Na].[C:18](OCC)(=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl.[CH2:29](O)[CH3:30]>C(OCC)(=O)C.C(Cl)(Cl)Cl>[CH2:29]([O:15][CH2:14][C:6]1[C:5]2[O:16][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:2][C:1](=[O:3])[C:4]=2[CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11]2)[CH3:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 7268Diethyl OxalateHCID 5360545SodiumHCID 21314614HCID 21314614, compound

Product 1

HCID 20304544HCID 20304544, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of step (b) (15.4 g) in ethanol (50 ml) was added to one of sodium (4.0 g) in ethanol (50 ml). To this mixture was added diethyl oxalate (50 g) and the whole mixture was heated at-reflux for 2 hours, then poured into a mixture of chloroform (500 ml) and concentrated HCl (100 ml). The organic layer was separated, evaporated to dryness and the residue was heated at reflux in ethanol (200 ml) containing concentrated hydrochloric acid (5 ml) for 2 hours. The solution was evaporated to dryness and the residue was taken up in ethyl acetate. This solution (was washed well with water, dried (MgSO4), filtered and the filtrate was evaporated to dryness leaving an oil. This was dissolved in a small amount of ethyl acetate and the solution was allowed to crystallise to give the title ester 6.3 g (30%), mp 115°-6°. It should be noted that under these reaction conditions the hydroxymethyl group of the starting naphthol has been converted into an ethoxymethyl grouping.

Workup

  1. temperaturethe whole mixture was heated
  2. temperatureat-reflux for 2 hours
  3. customThe organic layer was separated
  4. customevaporated to dryness
  5. temperaturethe residue was heated
  6. temperatureat reflux in ethanol (200 ml)
  7. additioncontaining concentrated hydrochloric acid (5 ml) for 2 hours
  8. customThe solution was evaporated to dryness
  9. washThis solution (was washed well with water
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe filtrate was evaporated to dryness
  13. customleaving an oil
  14. customto crystallise

Sources & evidence

ORD record
ord-fac79b839f3d48c284ea7f1cc38626fc
Source dataset
uspto-grants-1979_06
Patent number
US04159273

Reaction notes

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