Trimethyl orthoformate → 1-Methoxycyclooct-1-ene

HRID 542634Notes

Reaction equation

HRID 542634 reaction equation
[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:10](OC)(OC)OC>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:10][O:9][C:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 10403Cyclooctanone

Product 1

HCID 425867101-Methoxycyclooct-1-eneYield 75.2%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

In the presence of 0.2 g of para-toluenesulfonic acid, 16.5 g (0.13 mol) of cyclooctanone and 16.5 g (0.15 mol) of trimethyl orthoformate were stirred at room temperature for four hours. The resultant mixture was heated at 100° C. for 14 hours. The vacuum distillation of the mixture gave 13.7 g (75% in yield) of 1-methoxycyclooctene having a boiling point of 83° to 88° C./27 mmHg.

Workup

  1. distillationThe vacuum distillation of the mixture

Sources & evidence

ORD record
ord-d8c3c6510c8842599f1bc0a69938ef31
Source dataset
uspto-grants-1987_04
Patent number
US04658055

Reaction notes

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