Acetic Acid → Methyl 6-fluoro-2-hydroxy-3,4-dihydro-1-naphthoate

HRID 1641039Notes

Reaction equation

[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:15](=[O:20])[CH2:14][CH2:13]2.C(O)(=O)C>C1(C)C=CC=CC=1.O>[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:3]([O:6][CH3:7])=[O:8])=[C:15]([OH:20])[CH2:14][CH2:13]2

Participants

Conditions

Temperature: 0 °C

Procedure

12.66 g (316 mmol) of 60% sodium hydride in oil, 900 ml of toluene and 17.69 ml (210 mmol) of dimethyl carbonate are introduced into a 2 l reactor. The reaction mixture is stirred at reflux for 1 h. A solution of 19 g (115 mmol) of 6-fluoro-3,4-dihydro-1H-naphthalen-2-one in 350 ml of toluene is subsequently added. The reaction mixture is heated at reflux for 24 h. The reaction mixture is subsequently cooled to 0° C. and then acidified by addition of 114 ml of acetic acid. 114 ml of water are added and the separated organic phase is separated by settling and washed with two times 150 ml of water and then with 100 ml of a saturated aqueous sodium chloride solution. The organic phase is subsequently dried over magnesium sulphate and then concentrated under reduced pressure to result in 26.1 g of a product which is used as is in the following stage.

Workup

temperatureat reflux for 1 h
temperatureThe reaction mixture is heated
temperatureat reflux for 24 h
customthe separated organic phase is separated
washwashed with two times 150 ml of water
dry with materialThe organic phase is subsequently dried over magnesium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-959164c965a24b5383bcc08d72cecf07
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114899B2

Reaction notes

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