Trimethyl orthoformate → 1-Methoxycyclooct-1-ene

HRID 231923Notes

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>>[CH3:10][O:9][C:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

Reactant 2

HCID 9005Trimethyl orthoformate

HCID 10403Cyclooctanone

Product 1

HCID 425867101-Methoxycyclooct-1-eneYield 75.2%

Procedure

In the presence of 0.2 g of paratoluenesulfonic acid, 16.5 g (0.13 mol) of cyclooctanone and 16.5 g (0.15 mol) of trimetyl 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% yield) of 1-methoxycyclooctene having a boiling point of 83° to 88° C./27 mmHg.

Workup

distillationThe vacuum distillation of the mixture

Sources & evidence

ORD record: ord-d8bcfd50b48d4c85aa7b6f9922f40df1
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04849535

Reaction notes

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