Sodium Hydroxide → HCID 20536186, compound

HRID 1155964Notes

Reaction equation

HRID 1155964 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]([OH:11])[C:8]([CH3:13])([CH3:12])[C:7]=2[CH:14]=1)#[N:2].[OH-].[Na+].[BH4-].[Na+]>CO.O>[OH:10][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:14][C:7]=1[C:8]([CH3:13])([CH3:12])[CH2:9][OH:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 205362002-Hydroxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-carbonitrile

Product 1

HCID 20536186HCID 20536186, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-Cyano-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran (2.0 g), prepared as in Example 10, was dissolved in methanol (10 ml) and added to sodium hydroxide (1.7 g) in water (25 ml) at 10°-15° C. with stirring. To this solution was added sodium borohydride (0.5 g), and the mixture was stirred at ambient temperature for 11/2 hours. After acidification with hydrochloric acid (6 ml) at 8°-12° C., the mixture was filtered and the product washed with water and dried yielding 1.8 g. Recrystallisation from toluene gave 1.2 g of product, mp 129°-130° C.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 11/2 hours
  2. filtrationAfter acidification with hydrochloric acid (6 ml) at 8°-12° C., the mixture was filtered
  3. washthe product washed with water
  4. customdried
  5. customyielding 1.8 g
  6. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-cb19851771cc4e55a5e1d259c3c336ce
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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