Monobenzone → p-Benzyloxy-(1-methylheptyloxy)benzene

HRID 979417Notes

Reaction equation

HRID 979417 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C1(C)C=CC(S(O[CH:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(=O)=O)=CC=1.CCCCCC[C@@H](O)C>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7638MonobenzoneHCID 14798Sodium HydroxideHCID 2723888(+)-2-OctanolHCID 3912199p-Toluenesulfonic acid 1-methylheptyl ester

Product 1

HCID 13878908p-Benzyloxy-(1-methylheptyloxy)benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Benzyloxyphenol (50 g), ethanol (150 ml) and 50% NaOH aqueous solution (25 g) were mixed with stirring, followed by pouring in the mixture, optically active 1-methylheptyl p-toluenesulfonate derived from S-(+)-2-octanol, heating the mixture under reflux for 4 hours, distilling off most of ethanol, extracting with toluene, washing with acid, alkali and water, drying, concentrating and purifying the concentrate according to column chromatography with activated alumina (150 g) to obtain oily p-benzyloxy-(1-methylheptyloxy)benzene (68.6 g), which was then subjected to hydrogenolysis with 5% Pd-C catalyst in ethanol, followed by removing the catalyst, concentrating the solution and subjecting the concentrate to vacuum distillation to obtain oily p-(1-methylheptyloxy)phenol (IIIa-2) (30.7 g) having a b.p. of 129°-130.5° C./0.5 Torr.

Workup

  1. temperatureheating the mixture
  2. temperatureunder reflux for 4 hours
  3. distillationdistilling off most of ethanol
  4. extractionextracting with toluene
  5. washwashing with acid
  6. dry with materialalkali and water, drying
  7. concentrationconcentrating
  8. custompurifying the concentrate

Sources & evidence

ORD record
ord-c83ce745fc6b4b1eaea688b421f25721
Source dataset
uspto-grants-1987_05
Patent number
US04668427

Reaction notes

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