Monobenzone → HCID 67933334, compound

HRID 845712Notes

Reaction equation

HRID 845712 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:18][C@@H:19]([CH2:36][CH3:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]OS(C1C=CC(C)=CC=1)(=O)=O>O.C(O)C>[CH3:18][C@@H:19]([CH2:36][CH3:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:17][C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7638MonobenzoneHCID 14798Sodium HydroxideHCID 13463456HCID 13463456, compound

Product 1

HCID 67933334HCID 67933334, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of NaOH (40 g) dissolved in water (18 ml) was added to a solution of p-benzyloxyphenol (12 g, 0.060 mol) dissolved in ethanol (60 ml), followed by dropwise adding to the mixture, (S)-6-methyloctyl-p-toluenesulfonate (16.7 g, 0.055 mol) obtained above, refluxing the resulting mixture for 12 hours, distilling off ethanol after completion of the reaction, extracting the residue with toluene, washing the resulting ortanic layer with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution, further with water until the washing water became neutral, drying the layer, distilling off the organic solvent to obtain an oily product, and subjecting this product to column chromatography with activated alumina (17 g) to obtain (S)-p-benzyloxyphenyl 6-methyloctyl ether (15 g), dissolving this product (15 g, 0.046 mol) in ethanol (43 ml), subjecting the solution to hydrogenolysis in the presence of paradium-carbon (1.5 g) to obtain (S)-p-6-methyloctyloxyphenol (XII) (8.2 g).

Workup

  1. customobtained above,
  2. temperaturerefluxing the resulting mixture for 12 hours
  3. distillationdistilling off ethanol
  4. customafter completion of the reaction
  5. extractionextracting the residue with toluene
  6. washwashing the resulting ortanic layer with 6N-hydrochloric acid
  7. customdrying the layer
  8. distillationdistilling off the organic solvent
  9. customto obtain an oily product

Sources & evidence

ORD record
ord-324c0c035898408aa7c3046226cd0054
Source dataset
uspto-grants-1988_07
Patent number
US04759869

Reaction notes

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