Hydrochloric Acid → (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}phenyl)prop-2-enoic acid

HRID 511722Notes

Reaction equation

[F:1][C:2]([F:30])([O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13]C)=[O:12])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[F:1][C:2]([F:30])([O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 55 °C

Procedure

23 g (53.4 mmol) of methyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}-phenyl)prop-2-enoate is dissolved in 400 ml of dioxane. 30 ml of NaOH (30%) diluted in 250 ml of water is added to the solution. The mixture is heated to 55° C. for 2 hours. The mixture is cooled to room temperature and is carefully acidified to pH=2 with a HCl solution (25%) and is stirred for 15 min. The product is filtrated off and dried at room temperature under vacuum for 10 h to give 18 g of (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]-methyl}phenyl)-prop-2-enoic acid as a colourless powder.

Workup

additionis added to the solution
temperatureThe mixture is cooled to room temperature
filtrationThe product is filtrated off
customdried at room temperature under vacuum for 10 h

Sources & evidence

ORD record: ord-cf95aecb48e9451294674ec625e9f688
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09097938B2

Reaction notes

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