Dimethyl Carbonate → HCID 70400379, compound

HRID 483073Notes

Reaction equation

HRID 483073 reaction equation
C([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:29])[CH2:17][CH:18]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:19][CH2:20][CH:21]([O:23][CH3:24])[CH3:22])=[CH:12][CH:11]=1)CCCCCCCC.OC(CCC(CC(C1C=CC=CC=1)=O)CCCC)C.COC(OC)=O>>[CH3:24][O:23][CH:21]([CH2:20][CH2:19][CH:18]([CH2:17][C:16]([C:13]1[CH:12]=[CH:11][CH:10]=[CH:15][CH:14]=1)=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])[CH3:22]

Participants

4

Reactant 3

HCID 12021Dimethyl CarbonateHCID 53924493HCID 53924493, compoundHCID 86740691HCID 86740691, compound

Product 1

HCID 70400379HCID 70400379, compoundYield 88%

Procedure

A mixture of the above anisole (31 g) and glacial acetic acid (15 g) was heated to 70° C. for five hours, during which time a steady stream of BF3 was added. After cooling the reaction mixture, it was dissolved in 200 mL methylene chloride and washed with 200 mL water. The organic layer was dried (MgSO4) and the solvent was removed under vacuum to give 32.5 g of a red oil identified as a mixture of p-nonyl 2-methoxy-5-nonylacetophenone (major product) and 2-hydroxy-5-nonylacetophenone. To ensure complete conversion to the methoxyketone, the product mixture was re-alkylated by the phase transfer reaction described above. Work-up of the reaction mixture yielded 31.5 g (88%) of 2-methoxy-5-nonylacetophenone.

Workup

  1. customthe product mixture was re-alkylated by the phase transfer reaction

Sources & evidence

ORD record
ord-d1687d3892894e1ca41d1c4c487586ba
Source dataset
uspto-grants-1986_03
Patent number
US04578250

Reaction notes

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