Hydrochloric Acid → (3-Chloro-2-methylphenyl)methanol

HRID 2390031Notes

Reaction equation

HRID 2390031 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].Cl>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 820103-Chloro-2-methylbenzoic acid

Product 1

HCID 13169022(3-Chloro-2-methylphenyl)methanolYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.70 g of 3-chloro-2-methylbenzoic acid in 20 mL of THF was added dropwise 20 mL of a borane/THF complex under ice-cooling, followed by stirring at room temperature for 2 hours. After completion of the reaction, 1 N hydrochloric acid was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1.52 g (yield 97%) of a title compound as a white crystal.

Workup

  1. temperaturecooling
  2. additionwas added to the reaction liquid
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f408fc813bcc47139652cd15c906a7da
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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