Hexanoic Acid → Hexanoyloxymethyl p-nitrophenyl carbonate

HRID 2073331Notes

Reaction equation

HRID 2073331 reaction equation
[C:1](=[O:15])([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[O:2][CH2:3]I.[C:16]([OH:23])(=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C1C=CC=CC=1.C([O-])(=O)CCCCC.[Ag+]>[C:1](=[O:15])([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[O:2][CH2:3][O:23][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 8892Hexanoic AcidHCID 15053075Carbonic acid, iodomethyl 4-nitrophenyl ester

Product 1

HCID 15053076Hexanoyloxymethyl p-nitrophenyl carbonateYield 116.2%

Reagents, catalysts & solvents 2

HCID 14402368Silver hexanoateCatalystHCID 241BenzeneSolvent

Procedure

A solution of 0.25 g of iodomethyl p-nitrophenyl carbonate and 0.5 g hexanoic acid was heated to reflux in benzene with 0.5 g of silver hexanoate. After two hours the reaction mixture was filtered, and the filtrate was washed successively with aqueous sodium bicarbonate and water. After drying over sodium sulfate, the solvent was evaporated to furnish hexanoyloxymethyl p-nitrophenyl carbonate as a light yellow liquid (0.28 g). IR (film) 1775 (C=O). NMR (CDCl3) 0.9 (t, 3H, J=7 Hz, Me), 1.1-2.0 (m, 6H, (CH2)3), 2.41 (t, 2H, J=7 Hz, COCH2), 5.88 (s, 2H, OCH2O), 7.38 (d, 2H, J=10 Hz, aromatic), 8.21 (d, J=10 Hz, 2H, aromatic).

Workup

  1. filtrationAfter two hours the reaction mixture was filtered
  2. washthe filtrate was washed successively with aqueous sodium bicarbonate and water
  3. dry with materialAfter drying over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-85dff0f9804643baaa778be6ecb0af53
Source dataset
uspto-grants-1990_04
Patent number
US04916230

Reaction notes

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