HCID 18923484, compound → HCID 53810750, compound

HRID 1899973Notes

Reaction equation

HRID 1899973 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:9][CH:8]=[C:7]([Cl:15])[C:3]=1[C:4](O)=[O:5]>O1CCCC1>[Cl:1][C:2]1[C:10]([O:11][CH:12]([CH3:13])[CH3:14])=[CH:9][CH:8]=[C:7]([Cl:15])[C:3]=1[CH2:4][OH:5]

Participants

3

Reactant 1

HCID 18923484HCID 18923484, compound

Product 1

HCID 53810750HCID 53810750, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dichloro-3-isopropoxybenzoic acid (2.49 g) in tetrahydrofuran (30 ml) was added borane-methyl sulfide complex (2 ml, 10 Mol solution) through a syringe at ambient temperature. The mixture was refluxed for half an hour, cooled, and quenched with aqueous saturated ammonium chloride solution. The organic layer was dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give 2,6-dichloro-3-isopropoxybenzyl alcohol as a colorless oil (1.66 g).

Workup

  1. temperatureThe mixture was refluxed for half an hour
  2. temperaturecooled
  3. customquenched with aqueous saturated ammonium chloride solution
  4. customThe organic layer was dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f4c88ad0ec4f4170943c4a7346fa71f7
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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