O-Cresol → 1,10-Bis(4-hydroxy-3-methylphenyl)decane

HRID 342754

Reaction equation

HRID 342754 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([OH:22])(=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=O>>[OH:7][C:6]1[CH:5]=[CH:4][C:3]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([OH:22])=[C:1]([CH3:8])[CH:2]=2)=[CH:2][C:1]=1[CH3:8].[OH:7][C:6]1[CH:5]=[CH:4][C:3]([C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:3]2[CH:4]=[CH:5][C:6]([OH:7])=[C:1]([CH3:8])[CH:2]=2)=[O:22])=[CH:2][C:1]=1[CH3:8]

Participants

4

Reactant 2

HCID 335O-CresolHCID 5192Sebacic Acid

Product 2

HCID 545308101,10-Bis(4-hydroxy-3-methylphenyl)decaneHCID 545710481,10-Bis(4-hydroxy-3-methylphenyl)decane-1,10-dione

Conditions

Temperature
80 °C

Procedure

This was prepared by the method reported by Schlack and Koller in Aromatic aliphatic diketones. P Schlack and W Koller. Ger. 1,086,711 Aug. 11, 1960. The title compound was prepare by treatment of orthocresol (2.2 moles) with sebacic acid (1 mole) in the presence of polyphosphoric acid (3 moles). The mixture was stirred for 4 hrs at 80° C. and poured to ice-water after cooling. The precipitant was filtered, dissolved in ethyl acetate and washed with water three times. The solvent was evaporated to yield a crude 1,10-bis(4-hydroxy-3-methylphenyl)decane-1,10-dione which was then subjected to Clemmensen reduction to give the title compound.

Workup

  1. customThis was prepared by the method
  2. temperatureafter cooling
  3. filtrationThe precipitant was filtered
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water three times
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-116a6e421b2e46a3bc83e2cbd8661c88
Source dataset
uspto-grants-1999_01
Patent number
US05859067

Linked notes

Loading…