Propylene Oxide → 2-Naphthol Ether

HRID 1611466Notes

Reaction equation

HRID 1611466 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].[CH2:12]1[O:15][CH:13]1[CH3:14]>C1(C)C=CC=CC=1>[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].[CH3:14][CH2:13][O:15][CH2:12][CH3:1]

Participants

4

Reactant 2

HCID 6378Propylene Oxide2×HCID 86632-Naphthol

Product 1

HCID 197425842-Naphthol Ether

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a clean, dry stirred tank pressure vessel with nitrogen inlet is charged 1434.05 g (9.95 moles) of 2-Naphthol and 1445 mLs of Toluene. The vessel is purged with nitrogen and a catalytic amount (4.97 g) of BF3/Etherate Solution is charged. The temperature is raised to 110° C. and 2310.86 g (39.79 moles) of Propylene Oxide is added at a constant rate to keep the pressure inside the vessel below 50 psig. After all Propylene Oxide is added, the reaction mixture is allowed to react for an additional 3 hours after which the temperature is raised to 150° C. and the toluene is distilled off under nitrogen sparge. After the distillation of Toluene, the temperature is cooled to 110° C. and vacuum is applied for 1 hour.

Workup

  1. customTo a clean, dry
  2. customThe vessel is purged with nitrogen
  3. additiona catalytic amount (4.97 g) of BF3/Etherate Solution is charged
  4. customto react for an additional 3 hours after which the temperature
  5. temperatureis raised to 150° C.
  6. distillationthe toluene is distilled off under nitrogen
  7. customsparge
  8. distillationAfter the distillation of Toluene
  9. temperaturethe temperature is cooled to 110° C.

Sources & evidence

ORD record
ord-abc2c14f070945feb7ce52bbed5d2031
Source dataset
uspto-grants-2006_01
Patent number
US06987195B2

Reaction notes

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