2-Methyl-2-butanol → Heptylbenzene

HRID 13887

Reaction equation

HRID 13887 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[K+].C(O)(CC)(C)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 64052-Methyl-2-butanolHCID 123691-BromoheptaneHCID 66827Phenylboronic AcidHCID 23136641Di-tert-butyl(methyl)phosphanium tetraphenylborate(1-)HCID 23665647Potassium tert-butoxide

Product 1

HCID 14115HeptylbenzeneYield 89.1%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A 50-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.896 g (5 mmol) of n-heptyl bromide, 0.914 g (7.5 mmol) of phenylboronic acid, 0.056 g (0.25 mmol) of palladium (II) acetate, 1.683 g (15 mmol) of potassium tert-butoxide and 25 ml of tert-amyl alcohol were weighed in the flask, followed by stirring. Further, 0.240 g (0.5 mmol) of di-tert-butylmethylphosphonium tetraphenylborate obtained in Example B-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 25° C. for 24 hours. After the completion of the reaction, 20 ml of saturated sodium chloride solution was added, followed by separation. The organic phase was purified by column chromatography to afford 0.785 g of 1-phenylheptane (yield: 89 mol % based on n-heptyl bromide). The identification of the product was made by mass spectroscopy.

Workup

  1. customA 50-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 25° C. for 24 hours
  5. customAfter the completion of the reaction, 20 ml of saturated sodium chloride solution
  6. additionwas added
  7. customfollowed by separation
  8. customThe organic phase was purified by column chromatography

Sources & evidence

ORD record
ord-c25732fe82a044a998fee3f740d7f5f2
Source dataset
uspto-grants-2010_06
Patent number
US07728176B2

Linked notes

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