Eugenol → Methyl isoeugenol

HRID 273937

Reaction equation

C1(OC)C(=CC=C(C=1)CC=C)O.C1CCN2C(=NCCC2)CC1.C(=O)(OC)OC.[CH3:30][O:31][C:32]1[C:33]([O:41][CH3:42])=[CH:34][C:35]([CH2:38][CH:39]=[CH2:40])=[CH:36][CH:37]=1>>[CH3:30][O:31][C:32]1[C:33]([O:41][CH3:42])=[CH:34][C:35]([CH:38]=[CH:39][CH3:40])=[CH:36][CH:37]=1

Participants

Reactant 4

HCID 3314Eugenol2×

HCID 7127Methyleugenol

HCID 12021Dimethyl Carbonate

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 7128Methyl isoeugenolYield 86%

Conditions

Temperature: 150 °C

Procedure

15 mol of eugenol was charged into a pressure reactor, along with 0.2 mol of 1,8-diazabicyclo[5.4.0]-7-undecene and 16 mol of dimethyl carbonate. The reactor was sealed and was heated to 150° C. After 2 hr, complete conversion of the eugenol was shown to have occurred. After the distillation, 13 mol of eugenol methyl ether and 1 mol of isoeugenol methyl ether were obtained, corresponding to a yield of 86%, based on the starting amount of eugenol.

Workup

customThe reactor was sealed

Sources & evidence

ORD record: ord-aa17ab4a3614490ebb6e7a894b392bf6
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05387718

Linked notes

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