Ethanol → HCID 12422085, compound

HRID 1763420Notes

Reaction equation

HRID 1763420 reaction equation
C(O)C.[O:4]=[C:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]=2[CH2:8][CH2:7][CH2:6]1.[BH4-].[Na+]>CC(C)=O>[OH:4][CH:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]=2[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 12422084HCID 12422084, compound

Product 1

HCID 12422085HCID 12422085, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 200 ml. of ethanol is added 10.9 g. of ethyl 1,2,3,4-tetrahydro-1-oxo-5-naphthoate and while the solution is stirred at room temperature, 950 mg. of sodium borohydride is added. The mixture is stirred for 4 hours, after which 2 ml. of acetone is added. The mixture is further stirred for 30 minutes and, then, the solvent is distilled off under reduced pressure. Following the addition of 30 ml. of 2N hydrochloric acid, the residue is extracted with ethyl ether. The organic layer is washed with water and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the oily residue is purified by column chromatography on silica gel (100 g. silica gel; eluted with chloroform). The described procedure gives ethyl 1-hydroxy-1,2,3,4-tetrahydro-5-naphthoate as an oily product. Infrared absorption spectrum (neat)

Workup

  1. stirringThe mixture is further stirred for 30 minutes
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionthe addition of 30 ml
  4. extractionof 2N hydrochloric acid, the residue is extracted with ethyl ether
  5. washThe organic layer is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent is then distilled off under reduced pressure
  8. customthe oily residue is purified by column chromatography on silica gel (100 g. silica gel; eluted with chloroform)

Sources & evidence

ORD record
ord-b64a8db564664d529010883a2fa2ed51
Source dataset
uspto-grants-1978_09
Patent number
US04111997

Reaction notes

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