11-Benzyloxy-1-(3,4-dibenzyloxyphenyl)-1-undecanol → 4-(11-Hydroxyundecyl)benzene-1,2-diol

HRID 2290824Notes

Reaction equation

HRID 2290824 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27]CC2C=CC=CC=2)=[C:23]([O:35]CC2C=CC=CC=2)[CH:22]=1)O)C1C=CC=CC=1>C(O)(=O)C>[OH:35][C:23]1[CH:22]=[C:21]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH:26]=[CH:25][C:24]=1[OH:27]

Participants

3

Reactant 1

HCID 1355788511-Benzyloxy-1-(3,4-dibenzyloxyphenyl)-1-undecanol

Product 1

HCID 135578904-(11-Hydroxyundecyl)benzene-1,2-diolYield 68.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 40 ml of acetic acid was dissolved 4.4 g of 11-benzyloxy-1-(3,4-dibenzyloxyphenyl)-1-undecanol and the compound was catalytically reduced in the presence of 1 g of 10% palladium-carbon at room temperature and under atomospheric pressure until the absorption of hydrogen stopped. After the reaction was over, the catalyst was filtered off and after adding 300 ml of water to the filtrate, the product was extracted twice each time with 70 ml of ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off to provide a solid product. The solid product was recrystallized from 10 ml of a mixture of ethyl acetate and toluene (1:1) to provide 1.5 g of 11-(3,4-dihydroxyphenyl)-1-undecanol.

Workup

  1. customthe compound was catalytically reduced in the presence of 1 g of 10% palladium-carbon at room temperature and under atomospheric pressure until the absorption of hydrogen
  2. filtrationwas filtered off
  3. additionafter adding 300 ml of water to the filtrate
  4. extractionthe product was extracted twice each time with 70 ml of ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customto provide a solid product
  9. customThe solid product was recrystallized from 10 ml of a mixture of ethyl acetate and toluene (1:1)

Sources & evidence

ORD record
ord-97eedd8691d04d34881699f001b90392
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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