Hydrochloric Acid → HCID 20289613, compound

HRID 1414053Notes

Reaction equation

HRID 1414053 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH2:9][C:10]([OH:12])=[O:11])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O.[BH4-].[Na+].Cl>O1CCCC1>[CH3:14][O:13][C:6]1[C:7]([CH2:9][C:10]([OH:12])=[O:11])=[CH:8][C:3]([CH3:1])=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20289612HCID 20289612, compound

Product 1

HCID 20289613HCID 20289613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4 g of 2-Formyl-5-methoxy-4-biphenylacetic acid are dissolved in 300 ml of dry tetrahydrofuran and 2.5 g of sodium borohydride added. The reaction mixture is warmed to 80° for 40 minutes and, after cooling, dropped onto 150 g of ice, acidified with 2 N hydrochloric acid and extracted three times with ethyl acetate. The organic phases are washed with saturated brine, dried over Na2SO4 and concentrated. The residue is hydrogenated in 200 ml of ethyl acetate in the presence of 250 mg of Pd (10% on active charcoal) at a hydrogen pressure of 2 atmospheres. After three hours, the reaction mixture is filtered through talc and the filtrate evaporated. The product is recrystallized from ethyl acetate. M. pt. 127°-128°.

Workup

  1. temperatureThe reaction mixture is warmed to 80° for 40 minutes
  2. temperatureafter cooling
  3. extractionextracted three times with ethyl acetate
  4. washThe organic phases are washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. filtrationthe reaction mixture is filtered through talc
  8. customthe filtrate evaporated
  9. customThe product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-309d8e433d0945d29e9ec23cbe9aa075
Source dataset
uspto-grants-1981_02
Patent number
US04252817

Reaction notes

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