Acetic Acid → HCID 21465914, compound

HRID 1940197Notes

Reaction equation

HRID 1940197 reaction equation
C[O:2][C:3](=O)[CH:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13].[BH4-].[Li+].C(O)(=O)C>O1CCCC1>[N+:12]([C:6]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=1[CH:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[CH2:3][OH:2])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4148881Lithium borohydrideHCID 54256862HCID 54256862, compound

Product 1

HCID 21465914HCID 21465914, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture solution of α-(5-chloro-2-nitrophenyl)-2-chlorophenyl acetic acid methyl ester (26.3 g) and lithium borohydride (2 g) in tetrahydrofuran (200 ml) was stirred for 4 hours at room temperature. This mixture solution was added to a 20% aqueous solution of acetic acid (50 ml), which was extracted with acetic acid ethyl ester. The extract solution was washed with water, dried over anhydrous sodium sulfate and, then, the solvent was distilled off. The residual oily compound was purified by means of a silica-gel column chromatography to give 11.0 g of an oily compound.

Workup

  1. extractionwas extracted with acetic acid ethyl ester
  2. washThe extract solution was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residual oily compound was purified by means of a silica-gel column chromatography

Sources & evidence

ORD record
ord-7793b1cc039c496a91b95396ce95204d
Source dataset
uspto-grants-1997_12
Patent number
US05698691

Reaction notes

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