Sodium Hydroxide → p-Benzyloxy-(1-methylheptyloxy)benzene

HRID 868474Notes

Reaction equation

HRID 868474 reaction equation
C1(C(C2[C:14]([CH2:15][O:16][CH2:17][C:18]3[C:23](C4C(=CC=C(O)C=4)O)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=CC(=CC=1)O)O.[OH-].[Na+].[CH3:34][CH:35]([O:42]S(C1C=CC(C)=CC=1)(=O)=O)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C(O)C>[CH2:17]([O:16][C:15]1[CH:10]=[CH:11][C:12]([O:42][CH:35]([CH3:34])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:13][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3912199p-Toluenesulfonic acid 1-methylheptyl esterHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 13878908p-Benzyloxy-(1-methylheptyloxy)benzeneYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroquinone monobenzyl ether (50 g, 0.25 mol) was added to ethanol (250 ml), followed by adding to the solution, NaOH (12 g, 0.30 mol) and optically active p-toluenesulfonic acid 1-methyl-heptyl ester (78 g, 0.274 mol) prepared in Example 1 with stirring, refluxing the mixture for about 10 hours, distilling off ethanol, adding 6N-HCl (250 ml) and toluene (500 ml) to carry out extraction with toluene, washing the toluene layer with 2N-NaOH aqueous solution, then with water till the washing water became neutral, and distilling off the solvent to obtain optically active p-(1-methyl-heptyloxy)-phenol benzyl ether (76 g). This product (50 g, 0.16 mol) was dissolved in ethanol (100 ml) and reduced in the presence of Pd/C catalyst to obtain optically active p-(1-methylheptyloxy)-phenol (24 g) having a b.p. of 162°-165° C./6 mmHg.

Workup

  1. temperaturerefluxing the mixture for about 10 hours
  2. distillationdistilling off ethanol
  3. additionadding 6N-HCl (250 ml) and toluene (500 ml)
  4. extractionextraction with toluene
  5. washwashing the toluene layer with 2N-NaOH aqueous solution
  6. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-cbbf2cfbdb304ba88a8b1fbda2708e22
Source dataset
uspto-grants-1988_10
Patent number
US04780242

Reaction notes

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