Hydrochloric Acid → HCID 69696755, compound

HRID 897233Notes

Reaction equation

[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[Cl:20].[C:22]([C:28]([O:30]C)=[O:29])#[C:23][C:24]([O:26]C)=[O:25].[OH-].[Na+].Cl>O1CCOCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:21][C:23](=[CH:22][C:28]([OH:30])=[O:29])[C:24]([OH:26])=[O:25]

Participants

Conditions

Temperature: 90 °C

Procedure

Benzyltrimethylammonium hydroxide (1.5 mL of a 40% weight aqueous solution, 1.2%) was added to a solution of 3,4-dichlorophenol (20.0 g, 123 mmol), dimethyl acetylenedicarboxylate (16.6 mL, 135 mmol), and dioxane (230 mL) The dark, homogeneous mixture was heated at 90° C. for 1.5 h before the solution was cooled to ambient temperature, combined with 20% aqueous NaOH (100 mL), and warmed to 90° C. After an hour, the mixture was cooled to ambient temperature and combined with 2N aqueous HCl until the pH of the solution was neutral. White sediment was removed by filtration. The filtrate was combined with 2N aqueous HCl until acidic (pH=2). The resulting precipitate was collected by filtration, washed with copious water, and air-dried to provide the product (18.0 g, 53%) as a yellow solid. MS (APCI) m/z 275 [M−H]+; 1H NMR (300 MHz, DMSO-D6) δ ppm 6.64 (s, 1H) 6.95 (dd, J=8.82, 2.71 Hz, 1H) 7.25 (d, J=3.05 Hz, 1H) 7.57 (d, J=8.82 Hz, 1H).

Workup

temperaturewas cooled to ambient temperature
temperaturewarmed to 90° C
waitAfter an hour
temperaturethe mixture was cooled to ambient temperature
customWhite sediment was removed by filtration
filtrationThe resulting precipitate was collected by filtration
washwashed with copious water
customair-dried

Sources & evidence

ORD record: ord-14d0296e2bb54200895f1b1a33292fe2
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921821B2

Reaction notes

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