Water → 3,3-Dimethylhex-5-enyl 4-nitrobenzoate

HRID 1361911Notes

Reaction equation

HRID 1361911 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:6][CH:7]=[CH2:8])[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)([O-:19])=[O:18].O>ClCCl>[N+:17]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:5][CH2:4][CH2:3][C:2]([CH3:9])([CH3:1])[CH2:6][CH:7]=[CH2:8])=[O:25])=[CH:27][CH:28]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 114123903,3-Dimethylhex-5-en-1-ol

Product 1

HCID 669632843,3-Dimethylhex-5-enyl 4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

In a 500-mL, two-necked round-bottom flask, 3,3-dimethylhex-5-en-1-ol (5.30 g, 0.041 mol) and triethylamine (16 mL, 0.057 mol) were dissolved in dichloromethane (110 mL), and then the mixture was cooled, under nitrogen atmosphere, in an ice bath to 5° C. A dichloromethane (10 mL) solution of 4-nitrobenzoyl chloride (9.1 g, 0.049 mol) was added dropwise in 20 minutes. After the mixture had been stirred at 5-10° C. for 1 hour, water was added. The organic layer was washed with acid, water, brine, dried over sodium sulfate, and filtered. After evaporation of the solvent, the crude product was purified by column chromatography (silica gel; ethyl acetate/hexanes 1/9 as eluant) to give the title compound as a yellow liquid.

Workup

  1. washThe organic layer was washed with acid, water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customAfter evaporation of the solvent
  5. customthe crude product was purified by column chromatography (silica gel; ethyl acetate/hexanes 1/9 as eluant)

Sources & evidence

ORD record
ord-48c259dc3dfb4551b14bba745b23ca6e
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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