Toluene → 4-Hydroxy-4-methylpentyl 5-norbornene-2-carboxylate

HRID 1795731Notes

Reaction equation

HRID 1795731 reaction equation
[CH3:1][C:2]([OH:8])([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.C1(C)C=CC=CC=1.[CH:23]12[CH2:29][CH:26]([CH:27]=[CH:28]1)[CH2:25][CH:24]2[C:30](Cl)=[O:31]>O>[CH:23]12[CH2:29][CH:26]([CH:27]=[CH:28]1)[CH2:25][CH:24]2[C:30]([O:6][CH2:5][CH2:4][CH2:3][C:2]([OH:8])([CH3:7])[CH3:1])=[O:31]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 98233Bicyclo(2.2.1)hept-5-ene-2-carbonyl chlorideHCID 109862004-Methylpentane-1,4-diol

Product 1

HCID 221790144-Hydroxy-4-methylpentyl 5-norbornene-2-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 118 g of 4-methyl-1,4-pentanediol, 111 g of triethylamine and 400 ml of toluene at 20° C., 157 g of 5-norbornene-2-carbonyl chloride was added over one hour. After 5 hours of stirring, 200 ml of water was added to the reaction solution to stop the reaction whereupon the mixture separated. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was purified by vacuum distillation, collecting 214 g of 0.4-hydroxy-4-methylpentyl 5-norbornene-2-carboxylate (boiling point: 111–113° C./27 Pa, yield: 90%).

Workup

  1. customthe reaction whereupon the mixture
  2. customseparated
  3. washThe organic layer was washed with water and saturated sodium chloride water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuum
  6. distillationIt was purified by vacuum distillation
  7. customcollecting 214 g of 0

Sources & evidence

ORD record
ord-a3e462c9da31464493497ff34a57b857
Source dataset
uspto-grants-2006_04
Patent number
US07029822B2

Reaction notes

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