Sodium borohydride → HCID 118998220, compound

HRID 595208Notes

Reaction equation

HRID 595208 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:15])[CH2:9][C:8](=[O:10])[CH2:7][CH2:6][CH:5]1[C:11]([O:13][CH3:14])=[O:12]>CO.O>[OH:10][CH:8]1[CH2:7][CH2:6][CH:5]([C:11]([O:13][CH3:14])=[O:12])[C:4]([CH3:15])([CH3:3])[CH2:9]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58456348Cyclohexanecarboxylic acid, 2,2-diMethyl-4-oxo-, Methyl ester

Product 1

HCID 118998220HCID 118998220, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (6.19 g, 163 mmol) was added in portions at 0° C. to a solution of methyl 2,2-dimethyl-4-oxocyclohexanecarboxylate (10.0 g, 54.3 mmol) in methanol (200 mL). The mixture was stirred at room temperature for 30 minutes. Then the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give methyl 4-hydroxy-2,2-dimethylcyclohexanecarboxylate. 1H NMR (400 MHz, CDCl3): δ 3.89-3.84 (m, 1H), 3.65 (s, 3H), 2.21 (s, 1H), 1.79-1.73 (m, 1H), 1.70-1.68 (m, 3H), 1.49-1.35 (m, 2H), 1.06 (s, 6H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-965f94cbc200414da551c902cb79fe46
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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