Hydrochloric Acid → HCID 54567480, compound

HRID 2412944Notes

Reaction equation

HRID 2412944 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([CH3:12])[CH:10]=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[C:9]([CH3:12])[CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 367965HCID 367965, compoundHCID 4311764Sodium borohydride

Product 1

HCID 54567480HCID 54567480, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 113 g (0.69 mole) of 3-(4-fluorophenyl)-2-methyl-2-propen-1-al in 800 ml ethanol at 10° C. was added in portions 13.1 g (0.345 mole) of sodium borohydride. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The mixture was cooled in an ice bath while 350 ml of 1N hydrochloric acid was added dropwise to give a final pH of ~7. The mixture was diluted with 500 ml water and extracted three times with methylene chloride. The organic extracts were dried and concentrated and the residue distilled to give 56.1 g (49%) of colorless liquid, b.p. 68°-70° C. (0.15 mm).

Workup

  1. additionAfter the addition
  2. additionwas added dropwise
  3. customto give a final pH of ~7
  4. extractionextracted three times with methylene chloride
  5. customThe organic extracts were dried
  6. concentrationconcentrated
  7. distillationthe residue distilled

Sources & evidence

ORD record
ord-64a8517d68184e0ea50438cc3116d822
Source dataset
uspto-grants-1985_01
Patent number
US04495196

Reaction notes

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