Hydrochloric Acid → HCID 67749512, compound

HRID 1490261Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:13]([C:19]([O:21]C)=[O:20])#[C:14][C:15]([O:17]C)=[O:16].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[Na+].Cl>O1CCOCC1>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10]/[C:14](=[CH:13]\[C:19]([OH:21])=[O:20])/[C:15]([OH:17])=[O:16])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-(trifluoromethoxy)phenol (2.75 g, 12.5 mmole) and dimethyl acetylene dicarboxylate (1.69 ml, 13.7 mmole) in dioxane is treated with benzyltrimethylammonium hydroxide (0.15 ml, 40% aqueous) at room temperature under a nitrogen atmosphere, heated to 90°-95° C. (condensation complete by thin layer chromatographic analysis) cooled to 40° C. treated with sodium hydroxide (10 ml, 20% aqueous), heated at 90° C. for 1 hour and cooled to room temperature. The reaction mixture is treated with 10% aqueous HCl to pH 7 and filtered. The filtrate is acidified to about pH 1 with HCl to afford a yellow precipitate. The solid is filtered and dried to give the title product, 2.56 g (70% yield), mp 208°-210° C., identified by 1H, 13C and 19FNMR, mass spectral and elemental analyses.

Workup

temperatureheated to 90°-95° C.
custom(condensation complete by thin layer chromatographic analysis)
temperatureheated at 90° C. for 1 hour
temperaturecooled to room temperature
filtrationfiltered
customto afford a yellow precipitate
filtrationThe solid is filtered
customdried

Sources & evidence

ORD record: ord-9c2763c616f64d85afc60bebe25c21f0
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05681968

Reaction notes

Loading…