1,4-Cyclohexadiene → 4-(Hexyloxy)phenyl 4-hydroxybenzoate

HRID 64524Notes

Reaction equation

HRID 64524 reaction equation
C([O:8][C:9]1[CH:30]=[CH:29][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1.C1CC=CCC=1>[Pd].C1COCC1>[OH:8][C:9]1[CH:30]=[CH:29][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 672168004-(Hexyloxy)phenyl 4-(benzyloxy)benzoate

Product 1

HCID 200868254-(Hexyloxy)phenyl 4-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The 4-(hexyloxy)phenyl 4-(benzyloxy)benzoate obtained as described above (5.0 g, 12.4 mmol) and palladium on carbon (2.5 g in the wet state) were placed in a sealed container under a nitrogen atmosphere, and dehydrated THF was slowly added thereto. Then, 28 mL of 1,4-cyclohexadiene was carefully and slowly added thereto dropwise, while heating at 60° C. and stirring. After the addition, the mixture was further stirred for additional 3 hours at 60° C. After the mixture was cooled to room temperature, the mixture was filtered through Celite and the solvents were removed by distillation. Thereby, a white solid compound, 4-(hexyloxy)phenyl 4-hydroxybenzoate (3.8 g) was obtained.

Workup

  1. additionwas slowly added
  2. additionslowly added
  3. additionAfter the addition
  4. stirringthe mixture was further stirred for additional 3 hours at 60° C
  5. temperatureAfter the mixture was cooled to room temperature
  6. filtrationthe mixture was filtered through Celite
  7. customthe solvents were removed by distillation

Sources & evidence

ORD record
ord-503e37d638f64ce0a9f6e9692c583e50
Source dataset
uspto-grants-2016_09
Patent number
US09449732B2

Reaction notes

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