Water → Allyl 2-(3-nitrophenyl)acetate

HRID 1422596Notes

Reaction equation

HRID 1422596 reaction equation
[CH2:1](O)[CH:2]=[CH2:3].C(N(CC)CC)C.[N+:12]([C:15]1[CH:16]=[C:17]([CH2:21][C:22](Cl)=[O:23])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].[OH2:25]>>[N+:12]([C:15]1[CH:16]=[C:17]([CH2:21][C:22]([O:23][CH2:3][CH:2]=[CH2:1])=[O:25])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]

Participants

5

Reactant 4

HCID 962WaterHCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 5232253-Nitrobenzeneacetyl chloride

Product 1

HCID 86182979Allyl 2-(3-nitrophenyl)acetateYield 81%

Conditions

Temperature
11.5 °C

Procedure

To a solution of allyl alcohol (48.3 g, 56.5 ml, 831 mmol, Eq: 10) and triethylamine (12.6 g, 17.4 ml, 125 mmol, Eq: 1.5) at 0° C. was added 2-(3-nitrophenyl)acetyl chloride (intermediate B2a) (16.59 g, 83.1 mmol, Eq: 1.00) and the mixture was stirred at 0 to 23° C. for 2 h. Poured into water, extracted with ethyl acetate, washed organic layer with brine and dried over Na2SO4. Removal of the solvent in vacuum left a light brown oil, which was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the title compounds as a yellow liquid (14.89 g, 81%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed organic layer with brine
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a light brown oil, which
  6. customwas purified by silica gel flash chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-da938b9d82184e988bda895e857c1e1c
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

Loading…