Methanol → 7-Methoxycycloheptatriene

HRID 745288Notes

Reaction equation

HRID 745288 reaction equation
[B-](F)(F)(F)F.[CH:6]1[CH:12]=[CH:11][CH+:10][CH:9]=[CH:8][CH:7]=1.CO.[C:15](=O)(O)[O-:16].[Na+]>O>[CH3:15][O:16][CH:6]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 152926Cycloheptatrienylium, tetrafluoroborate(1-) (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 1371707-Methoxycycloheptatriene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-methoxy-1,3,5-cycloheptatriene can be produced from cycloheptatrienyl tetrafluoroborate (I) as described in Conrow K 1963 Organic Synthesis 43, 101. The reaction of (I) with methanol and sodium bicarbonate in water gives 7-methoxy-1,3,5-cycloheptatriene (II), (reference Conrow K1961, J. Am. Chem. Soc. 83,2342). The 1-methoxy-1,3,5-cycloheptriene can be made by the thermal isomerisation of (II) by heating at 150° for 2.5 hours in nitrogen atmosphere in the presence of antioxidants and absence of water, as described by T. NOZOE and K., Takahashi, Bull Chem. Soc. Japan, 38, 665, 1965. Pratt, J. T. Reaction of Cycloheptatriene, PHD Thesis, University of Washington, Seattle, Wash. 1964.

Workup

  1. customas described in Conrow K 1963 Organic Synthesis 43, 101

Sources & evidence

ORD record
ord-5a291a12543641bcadcb703bf3841894
Source dataset
uspto-grants-1986_07
Patent number
US04598096

Reaction notes

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