Potassium Carbonate → Methyl 3'-[3,4-bis(benzoyloxymethyl)benzyloxy]-biphenyl-4-carboxylate

HRID 2307543Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17]C)=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:19]([O:27][CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=1[CH2:37][O:38][C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:32]Br)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:19]([O:27][CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=1[CH2:37][O:38][C:39](=[O:46])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[CH2:32][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1 g (4.1 mmol) of ethyl 3′-hydroxybiphenyl-4-carboxylate, 1.98 g (4.5 mmol) of 3,4-bis(benzoyloxymethyl)benzyl bromide and 600 mg of potassium carbonate are dissolved in 40 mL of 2-butanone. The mixture is brought to reflux (80° C.) and then stirred for 4 hours. After cooling, the reaction medium is filtered and then concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, to give a white solid (m.p.=71-72° C.) (m=2.18 g; Y=88%).

Workup

temperatureAfter cooling
filtrationthe reaction medium is filtered
concentrationconcentrated under reduced pressure
customThe residue is purified by chromatography on a column of silica

Sources & evidence

ORD record: ord-58501bada0da4e4fa61a0a38672fce9b
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831106B1

Reaction notes

Loading…