Water → HCID 13135248, compound

HRID 354540Notes

Reaction equation

HRID 354540 reaction equation
[C:1]([C:3]1[C:4]([CH3:13])=[C:5]([C:9]([CH3:12])=[CH:10][CH:11]=1)[C:6](O)=[O:7])#[N:2].B.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:1]([C:3]1[C:4]([CH3:13])=[C:5]([CH2:6][OH:7])[C:9]([CH3:12])=[CH:10][CH:11]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 11430Potassium CarbonateHCID 13135247HCID 13135247, compound

Product 1

HCID 13135248HCID 13135248, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-cyano-2,6-dimethylbenzoic acid (8.11 grams, 0.049 mole) in tetrahydrofuran (100 ml) was cooled to 0°. Borane (48.7 grams, 0.049 mole) in tetrahydrofuran was added dropwise over a 20 minute period. The mixture was allowed to come to room temperature, and water was added. Potassium carbonate was added to separate the layers. The aqueous layer was extracted with diethyl ether. The extract was added to the organic phase, which was dried over magnesium sulfate, filtered, and the solvent evaporated to give (3-cyano-2,6-dimethylphenyl)methanol (2.93 grams).

Workup

  1. customto come to room temperature
  2. customto separate the layers
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. additionThe extract was added to the organic phase, which
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-b4710c02690841ae94fc02b6b2f138f5
Source dataset
uspto-grants-1983_03
Patent number
US04375476

Reaction notes

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