Catechol → 3-Nonylbenzene-1,2-diol

HRID 1722200Notes

Reaction equation

HRID 1722200 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].B(F)(F)F.CCOCC.[CH2:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[Cl-].[Na+]>>[CH2:18]([C:5]1[CH:6]=[CH:7][CH:8]=[C:1]([OH:2])[C:3]=1[OH:4])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 289Catechol3×HCID 5234Sodium ChlorideHCID 8000Boron trifluoride etherateHCID 312851-Nonene2×

Product 1

HCID 101927343-Nonylbenzene-1,2-diol

Conditions

Temperature
104 °C

Procedure

Into a 500ml, 3-neck reaction vessel was placed 64.8g (0.3125 moles) of catechol, after which time it was heated to 104° C. under a nitrogen flow. After the catechol was completely melted, 3.25g (5% based on the wt. of the catechol) of borontrifluoride-etherate was added dropwise, with stirring. After adding all of the catalyst, 63.2g (0.25 moles) of 1-nonene was added, dropwise to the reaction mixture, the rate of addition being adjusted so as to maintain a temperature of 130° C. After all of the 1-nonene was added, the resultant mixture was allowed to react for 3 hours, after which time 100ml of a 10% sodium chloride solution was added to the reaction mixture. The resultant mixture was then stirred for 15 minutes at 95° to 100° C., after which time the bottom layer was separated. The mixture was again stirred at 95° to 100° C. for 15 minutes, after which time the bottom layer was again separated. The organic layer was then isolated to obtain a viscous, brown oil of the formula ##STR6##

Workup

  1. additionwas added dropwise
  2. additionwas added, dropwise to the reaction mixture
  3. additionthe rate of addition
  4. temperatureto maintain a temperature of 130° C
  5. customto react for 3 hours
  6. customafter which time the bottom layer was separated
  7. stirringThe mixture was again stirred at 95° to 100° C. for 15 minutes
  8. customafter which time the bottom layer was again separated
  9. customThe organic layer was then isolated
  10. customto obtain a viscous, brown oil of the formula

Sources & evidence

ORD record
ord-df5014718e8e4939be52e1b41123ab6c
Source dataset
uspto-grants-1989_08
Patent number
US04855075

Reaction notes

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