Benzyl Alcohol → tert-Butyl-3-aminobenzoate

HRID 1081261Notes

Reaction equation

HRID 1081261 reaction equation
[N+](C1C=C(C[C:11]([OH:13])=[O:12])C=CC=1)([O-])=O.[CH2:14](O)[C:15]1[CH:20]=CC=C[CH:16]=1.CN[C:24]1(NC)[CH:29]=[CH:28][N:27]=[CH:26][CH2:25]1.[CH3:32]N(C)CCCN=C=NCC>ClCCl>[C:15]([O:13][C:11](=[O:12])[C:26]1[CH:25]=[CH:24][CH:29]=[C:28]([NH2:27])[CH:32]=1)([CH3:20])([CH3:16])[CH3:14]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 158763-Nitrophenylacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 865890494,4-Dimethylaminopyridine

Product 1

HCID 2737408tert-Butyl-3-aminobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-nitrophenylacetic acid (5 g), benzyl alcohol (2.9 ml) and 4,4-dimethylaminopyridine (300 mg) in dry dichloromethane (50 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (7.4 g). The resulting yellow mixture was stirred at 23° for 3 days whereupon the solvent was removed in vacuo. The residue was partitioned between water (100 ml) and ethyl actate (100 ml) and the organic phase washed with water (2×100 ml) and saturated brine (100 ml) then dried and evaporated. The residue was chromatographed with hexane-EA (4:1) as eluent then again with isohexane-DCM (1:1) as eluent to give the title compound (2.05 g) as a pale yellow oil.

Workup

  1. customwas removed in vacuo
  2. customThe residue was partitioned between water (100 ml) and ethyl actate (100 ml)
  3. washthe organic phase washed with water (2×100 ml) and saturated brine (100 ml)
  4. customthen dried
  5. customevaporated
  6. customThe residue was chromatographed with hexane-EA (4:1) as eluent

Sources & evidence

ORD record
ord-b7f00857342d4653b4f6aec99883705d
Source dataset
uspto-grants-1996_12
Patent number
US05585376

Reaction notes

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