Tetralin → Naphthalene

HRID 1981110Notes

Reaction equation

HRID 1981110 reaction equation
C(O)(=O)C[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=O.C1C2C(=CC=CC=2)CCC1.CC([O-])=O.[K+].C(OC1C2C(=CC=CC=2)C=CC=1)(=O)CCCCCCCCCCC([O-])=O>CC([O-])=O.CC([O-])=O.[Pd+2].O.CCCCCCC>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 8404TetralinHCID 12736Dodecanedioic AcidHCID 517044Potassium AcetateHCID 20399698HCID 20399698, compound

Product 1

HCID 931Naphthalene

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8900HeptaneSolvent

Conditions

Temperature
178 °C

Procedure

The procedure of Example 1 was repeated using 70 g (304 mmols) of dodecanedioic acid 13.2 g (100 mmols) of tetralin, 0.16 g (0.71 mmols) of Pd(OAc)2, 0.42 g (1.42 mmols) of Sb(OAc)3, 0.07 g (0.71 mmols) of KOAc and 5 ml heptane. Reaction mixture was heated and the temperature of the reaction was maintained at 178±2° C. Oxygen was bubbled continuously at a rate of 200 cc/min. Reaction was carried out for 3 hrs. during which time the water produced was removed azeotropically with heptane. Reaction mixture was analyzed by GLC which showed the formation of 3.65% (by wt.) naphthyl dodecanedioate. Only a trace of naphthalene formed in the reaction.

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. customOxygen was bubbled continuously at a rate of 200 cc/min
  4. customReaction
  5. customwas removed azeotropically with heptane
  6. customReaction mixture

Sources & evidence

ORD record
ord-e1e0b19b4d2d49ddae1313efb81b5f71
Source dataset
uspto-grants-1985_04
Patent number
US04512927

Reaction notes

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