Carbon Dioxide → 3-(1-Adamantyl)-4-methoxyethoxymethoxybenzoic acid

HRID 1957693Notes

Reaction equation

[C:1]12([C:11]3[CH:12]=[C:13](Br)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Mg].II.[C:28](=[O:30])=[O:29].[Cl-].[NH4+]>C1COCC1>[C:1]12([C:11]3[CH:12]=[C:13]([CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[C:28]([OH:30])=[O:29])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

Conditions

Temperature: -78 °C

Procedure

The above compound (a) (28.5 g, 72 mmol) was dissolved in 200 ml of THF. The solution obtained was added dropwise to magnesium (2.4 g, 100 mmol) and a crystal of iodine. After introduction, the mixture was heated at reflux for two hours, cooled to -78° C. and a stream of CO2 was passed therethrough for one hour. The reaction medium was permitted to warm to room temperature and was then poured into saturated aqueous ammonium chloride solution and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was triturated from hexane, filtered and dried. 15.5 g (60%) of the expected acid, having a melting point of 115°-6° C., were recovered.

Workup

customThe solution obtained
temperatureAfter introduction, the mixture was heated
temperatureat reflux for two hours
temperatureto warm to room temperature
extractionextracted with ethyl ether
customThe organic phase was separated out
dry with materialdried over magnesium sulfate
customevaporated
customThe residue obtained
customwas triturated from hexane
filtrationfiltered
customdried
customwere recovered

Sources & evidence

ORD record: ord-6edb50e4b9034309acaae9aa5a71a0bf
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05786379

Reaction notes

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