Phenol → HCID 173634, compound

HRID 1589673Notes

Reaction equation

HRID 1589673 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1([CH3:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][C:8]1[CH2:13][CH2:12][C@@H:11]([C:1]([CH3:6])=[CH2:2])[CH2:10][CH:9]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 1140Toluene

Product 1

HCID 173634HCID 173634, compoundYield 94%

Procedure

A 500 gram portion of phenol was dissolved in toluene and cooled to a temperature of less than 5° C. Gaseous nitrogen was bubbled through the phenol solution by means of a gas dispersion tube and a 30 cc. portion of redistilled BF3.(Et)2O was added. The solution changed color from light yellow to light red-brown. A 140 gram portion of d-limonene was slowly added by a dropping funnel while the solution was maintained at a temperature of less than 5° C. After maintaining this temperature overnight to allow completion of the reacion, the mixture was neutralized with 0.2N sodium hydroxide solution. The progress of the neutralization was followed by means of a color change (dark to light) of the reaction mixture. The reaction mixture was then steam distilled to remove the unreacted phenol. The mixture was cooled to room temperature, some of the water was removed by decantation and the remainder was removed by azetropic distillation using diethylether. The excess solvent was allowed to evaporate and the product was dried in an oven at 135° C. for 64 hours, yielding 236 grams of product (94% yield after correction for purity of the limonene).

Workup

  1. temperaturecooled to a temperature of less than 5° C
  2. customGaseous nitrogen was bubbled through the phenol solution by means of a gas dispersion tube
  3. addition(Et)2O was added
  4. additionA 140 gram portion of d-limonene was slowly added by a dropping funnel while the solution
  5. temperaturewas maintained at a temperature of less than 5° C
  6. temperatureAfter maintaining this temperature overnight
  7. distillationsteam distilled
  8. customto remove the unreacted phenol
  9. customsome of the water was removed by decantation
  10. customthe remainder was removed by azetropic distillation
  11. customto evaporate
  12. customthe product was dried in an oven at 135° C. for 64 hours

Sources & evidence

ORD record
ord-ec7dcc85a23c4e249d0e42e9255e251f
Source dataset
uspto-grants-1986_02
Patent number
US04573063

Reaction notes

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