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

HRID 511703
Notes
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Reaction equation

HRID 511703 reaction equation
[F:1][C:2]([F:30])([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)[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14]C)=[O:13])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[F:1][C:2]([F:30])([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)[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86676541methyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}-phenyl)prop-2-enoate

Product 1

HCID 86676542(2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoic acidYield 79.5%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

26 g (60.4 mmol) of methyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}-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 20 g of (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}-phenyl)prop-2-enoic acid as a colourless powder.

Workup

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

Sources & evidence

ORD record
ord-3a9d0fa2d116443f82cb2cc7a295b54b
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09097938B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes