Hydrochloric Acid → 5-Chloro-2-nitrobenzyl alcohol

HRID 256177Notes

Reaction equation

HRID 256177 reaction equation
B.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].Cl>O1CCCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH2:8][OH:9])[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 5560665-Chloro-2-nitrobenzyl alcoholYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of borane:tetrahydrofuran complex (25.8 g, 0.3 mole) in tetrahydrofuran (THF) (300 mL) was added dropwise to a stirred solution of 5-chloro-2-nitrobenzoic acid (50.0 g, 0.24 mole) in dry THF (400 mL) maintained at 0° C. under an atmosphere of nitrogen. After completion of the addition, the mixture was heated at 50° C. for 96 hours before being cooled in an ice bath. Hydrochloric acid (10% solution) was added dropwise and the mixture refluxed for 30 minutes. The THF was removed in vacuo and the residue extracted with dichloromethane (3×350 mL). Combined extracts were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and the solvent evaporated to give a solid (45 g, 100%), crystallization from chloroform-hexane gave 5-chloro-2-nitro-benzenemethanol (41.0 g, 91%) mp 79°-81° C.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was heated at 50° C. for 96 hours
  3. temperaturebefore being cooled in an ice bath
  4. temperaturethe mixture refluxed for 30 minutes
  5. customThe THF was removed in vacuo
  6. extractionthe residue extracted with dichloromethane (3×350 mL)
  7. washCombined extracts were washed with saturated sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent evaporated
  10. customto give
  11. customa solid (45 g, 100%), crystallization from chloroform-hexane

Sources & evidence

ORD record
ord-b2ea767f67b7434e8beafd874c5fa39f
Source dataset
uspto-grants-1987_10
Patent number
US04701459

Reaction notes

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