Methanol → 1-(2-Penten-1-yl)-2-naphthol

HRID 51171

Reaction equation

HRID 51171 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].CO.[CH:14]1[CH2:18][CH:17]=[CH:16][CH:15]=1.C1COCC1>CC(CC(C)=O)C>[CH2:16]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11])[CH:15]=[CH:14][CH2:18][CH3:17]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 7612CyclopentadieneHCID 8028TetrahydrofuranHCID 86632-Naphthol

Product 1

HCID 698872381-(2-Penten-1-yl)-2-naphthol

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Into a 2-liter flask having a stirrer, a condenser and a thermometer, 144 g of 2-naphthol, 200 g of methanol and 40 g of PTS were introduced, and a solution of mixture of 66 g of cyclopentadiene and 60 g of methanol was added dropwise over a period of 3 hours while stirring the mixture at room temperature, followed by further stirring for 4 hours at room temperature. To the reaction solution thus obtained, THF and MIBK were added, and the resultant solution was washed with 200 ml of an aqueous 10% sodium hydroxide solution five times, and thereafter further washed with water until it turned neutral, followed by removal of the solvent using an evaporator. The results of analysis by GPC thereof are shown in FIG. 11. Its yield determined by GPC was 90% (area ratio). An NMR spectrum of the 1-(2-penten-1-yl)-2-naphthol obtained is shown in FIG. 12.

Workup

  1. customInto a 2-liter flask having
  2. additionwas added dropwise over a period of 3 hours
  3. stirringby further stirring for 4 hours at room temperature
  4. customTo the reaction solution thus obtained
  5. washthe resultant solution was washed with 200 ml of an aqueous 10% sodium hydroxide solution five times
  6. washfurther washed with water until it
  7. customfollowed by removal of the solvent
  8. customan evaporator
  9. customThe results of analysis by GPC
  10. customIts yield

Sources & evidence

ORD record
ord-6f961dfb283f4d78b6133c6ade4457f0
Source dataset
uspto-grants-2004_03
Patent number
US06713589B2

Linked notes

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