Methanol → HCID 66901644, compound

HRID 1692385Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH:5]=[C:6]([CH3:11])[C:7]=1[C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[CH3:27]O>>[CH3:27][O:9][C:8]([C:7]1[C:6]([CH3:11])=[CH:5][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)=[CH:3][C:2]=1[OH:1])=[O:10]

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 66901582HCID 66901582, compound

Product 1

HCID 66901644HCID 66901644, compoundYield 45%

Procedure

A solution of 2.20 g (7.40 mmol) of 3-hydroxy-5-methyl-3′-trifluoromethyl-biphenyl-4-carboxylic acid in 70 ml of MeOH was treated at RT with 0.84 ml=1.53 g (14.9 mmol) of sulfuric acid (95%) and 0.5 g of molecular sieves (0.4 nm) and the reaction mixture was heated at reflux for 72 hours. It was then cooled down to RT, filtered and the residue was washed with MeOH. The filtrate was evaporated and this residue was dissolved in CH2Cl2 and poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (heptane/EtOAc 4:1) to give 1.04 g (45%) of the title compound as colorless solid. MS: 310.0 (M+).

Workup

temperaturethe reaction mixture was heated
temperatureat reflux for 72 hours
filtrationfiltered
washthe residue was washed with MeOH
customThe filtrate was evaporated
dissolutionthis residue was dissolved in CH2Cl2
additionpoured
extractionextracted twice with CH2Cl2
washthe organic phases were washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was purified by flash column chromatography (heptane/EtOAc 4:1)

Sources & evidence

ORD record: ord-7543c8efd83941eb89dd059c7859c944
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153805B2

Reaction notes

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