Methanol → HCID 12266617, compound

HRID 373369Notes

Reaction equation

HRID 373369 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([CH3:13])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:14].CO.O1CCCC1.[BH4-].[Na+]>CC(C)=O>[CH3:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([CH3:13])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[OH:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 12266612HCID 12266612, compound

Product 1

HCID 12266617HCID 12266617, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4,7-dimethyl-6-methoxy-1-indanone (7.0 g) in a mixed solvent of methanol (100 ml) and tetrahydrofuran (50 ml) was added sodium borohydride (1.2 g) at 0° C. and then the mixture was stirred at room temperature for 1 hour. Acetone (10 ml) was added and the solvent was distilled off under reduced pressure. Water (50 ml) and ethyl acetate (50 ml) were added and the organic layer was washed with water and saturated saline. The organic layer was dried with anhydrous magnesium sulfate and the solvent was removed under reduced pressure to obtain 4,7-dimethyl-6-methoxy-1-indanol (7.0 g) (Compound A-14). The physical properties and NMR spectrum data thereof are shown in Table 1.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater (50 ml) and ethyl acetate (50 ml) were added
  3. washthe organic layer was washed with water and saturated saline
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d2b070b4867440c895c5c858898841d1
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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