Veratrole → Bis(3,4-dimethoxyphenyl)methanone

HRID 849282Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:16](O)=[O:17]>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:9][CH3:10])[C:16]([C:15]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:13]([O:12][CH3:11])[CH:14]=1)=[O:17]

Participants

Conditions

Temperature: 60 °C

Procedure

16.92 g (120 mmol) of 1,2-dimethoxybenzene and 22.08 g (120 mmol) of 3,4-dimethoxybenzoic acid were stirred in 100 g of polyphosphoric acid (d=2.1 g/ml) at 80° C. for 30 min. The reaction mixture was then cooled to 60° C., and 250 ml of water was added dropwise over the course of 30 min. The resulting mixture was further cooled using ice, and the resulting precipitate was filtered off, washed with 2×60 ml of water and finally dried under reduced pressure to give 35.7 g of a reddish product. The yield of the product was 98 percent of theory.

Workup

temperatureThe resulting mixture was further cooled
filtrationthe resulting precipitate was filtered off
washwashed with 2×60 ml of water
customfinally dried under reduced pressure

Sources & evidence

ORD record: ord-5c20f95522384bb786959f2a842f63ba
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011178

Reaction notes

Loading…