Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate → 4-Hydroxy-4-methylpentyl 5-norbornene-2-carboxylate

HRID 1835966Notes

Reaction equation

HRID 1835966 reaction equation
[CH3:1][C:2]([OH:8])([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[CH:9]12[CH2:15][CH:12]([CH:13]=[CH:14]1)[CH2:11][CH:10]2[C:16](OC)=[O:17]>C[O-].[Na+].C1(C)C=CC=CC=1>[CH:9]12[CH2:15][CH:12]([CH:13]=[CH:14]1)[CH2:11][CH:10]2[C:16]([O:6][CH2:5][CH2:4][CH2:3][C:2]([OH:8])([CH3:7])[CH3:1])=[O:17]

Participants

5

Reactant 2

HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 109862004-Methylpentane-1,4-diol

Product 1

HCID 221790144-Hydroxy-4-methylpentyl 5-norbornene-2-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 118 g of 4-methyl-1,4-pentanediol, 173 g of methyl 5-norbornene-2-carboxylate, 1.4 g of sodium methoxide and 400 ml of toluene was heated under reflux for 5 hours while distilling off the methanol which formed during the reaction. The reaction solution was cooled, washed with saturated sodium bicarbonate water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was purified by vacuum distillation, collecting 221 g of 4-hydroxy-4-methylpentyl 5-norbornene-2-carboxylate (yield: 93%). The physical data of this product were in good coincidence with those of Synthesis Example 1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. distillationwhile distilling off the methanol which
  4. customformed during the reaction
  5. temperatureThe reaction solution was cooled
  6. washwashed with saturated sodium bicarbonate water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuum
  9. distillationIt was purified by vacuum distillation

Sources & evidence

ORD record
ord-b64690e674fb43fbb39d6b74b5a246ab
Source dataset
uspto-grants-2004_08
Patent number
US06774258B2

Reaction notes

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