Ethyl Acetate → HCID 53679561, compound

HRID 2418400Notes

Reaction equation

HRID 2418400 reaction equation
[BH4-].[Na+].[B].[N+:4]([C:7]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10])([O-:6])=[O:5].C(OCC)(=O)C>O1CCCC1.O>[N+:4]([C:7]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:14][CH:13]=[CH:12][C:8]=1[CH2:9][OH:10])([O-:6])=[O:5]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 5462311BoronHCID 20446304HCID 20446304, compound

Product 1

HCID 53679561HCID 53679561, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (4.4 g) and boron trifluoridediethyl ether (23.7 ml) were added to a solution of 2-nitro-3-(2-chlorophenoxy)benzoic acid (11.3 g) in dried tetrahydrofuran (100 ml), and the mixture was stirred for 3 hrs. at room temperature. To the reaction mixture were added ethyl acetate (200 ml) and water (200 ml), and the mixture was filtered. The ethyl acetate layer was separated from the filtrate, washed with aqueous sodium bicarbonate and saline, dried and then evaporated in vacuo. The oily residue (15.1 g) was subjected to column chromatography on silica gel (150 g) and eluted with methylene chloride to give 2-nitro-3-(2-chlorophenoxy)benzyl alcohol (10.5 g).

Workup

  1. customat room temperature
  2. filtrationthe mixture was filtered
  3. customThe ethyl acetate layer was separated from the filtrate
  4. washwashed with aqueous sodium bicarbonate and saline
  5. customdried
  6. customevaporated in vacuo
  7. washeluted with methylene chloride

Sources & evidence

ORD record
ord-cae99080cf494a6b8e9c1c5c265933f6
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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