Triethylamine → METHYL 3-(HYDROXYMETHYL)-5-NITROBENZOATE

HRID 1531939

Reaction equation

HRID 1531939 reaction equation
Cl[C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:3].[BH4-].[Na+].C(N(CC)CC)C>O1CCOCC1>[OH:3][CH2:2][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74774Methyl 3-(chlorocarbonyl)-5-nitrobenzoateHCID 4311764Sodium borohydride

Product 1

HCID 10703703METHYL 3-(HYDROXYMETHYL)-5-NITROBENZOATE

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of the product from step (i) (46.54 g) and sodium borohydride (13.01 g) in 1,4-dioxane (200 ml) was heated at reflux for 17 hours. The mixture was cooled and treated with triethylamine (27.9 ml), poured onto ice-water and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and evaporated. The product was recrystallised from isohexane. Yield 19.38 g.

Workup

  1. temperatureat reflux for 17 hours
  2. temperatureThe mixture was cooled
  3. additionpoured onto ice-water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated
  7. customThe product was recrystallised from isohexane

Sources & evidence

ORD record
ord-8ae2dc45fa73405cbbda1d2570d69ebf
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Linked notes

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