Cyclohexene → 7-Decyl-2-methylnaphthalen-1-ol

HRID 1583495Notes

Reaction equation

HRID 1583495 reaction equation
C(O[CH:10]=[C:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:16][CH:17]=2)[C:12]1=[O:31])(=O)C1C=CC=CC=1.C1CCCCC=1>[Pd]>[CH2:21]([C:15]1[CH:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([CH3:10])=[C:12]2[OH:31])=[CH:17][CH:16]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 8079CyclohexeneHCID 53837272HCID 53837272, compound

Product 1

HCID 135480347-Decyl-2-methylnaphthalen-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture of 2-benzoyloxymethylene-7-n-decyl-1-tetralone (14 g, 33.5 mmoles) and Pd/C (3.5 g) under inert atmosphere was added cyclohexene (175 mL). The mixture was heated to reflux while maintaining the inert atmosphere. The conversion of starting material to product was determined by TLC after 3 hours. After all the starting material reacted, the mixture was cooled down to RT. The catalyst was removed by filtration and washed twice with 50 mL hot toluene. The combined filtrate was evaporated to a small volume. The product was purified with a Prep-500 silica gel column (a high pressure silica gel preparative column, obtained from Waters Association, Milford, MA). Toluene was used as the mobile phase. The product fractions were pooled and evaporated to dryness under vacuum overnight. Cream white solid (9.0 g; 90% yield) was recovered. The melting point was 65°-67° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturewhile maintaining the inert atmosphere
  4. customAfter all the starting material reacted
  5. customThe catalyst was removed by filtration
  6. washwashed twice with 50 mL hot toluene
  7. customThe combined filtrate was evaporated to a small volume
  8. customThe product was purified with a Prep-500 silica gel column (a high pressure silica gel preparative column
  9. customevaporated to dryness under vacuum overnight
  10. customCream white solid (9.0 g; 90% yield) was recovered

Sources & evidence

ORD record
ord-4fc8fcc4d0bd4bc8843504bf0f435e06
Source dataset
uspto-grants-1985_11
Patent number
US04552697

Reaction notes

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