Hydrochloric Acid → (Z)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-methoxy-acrylic acid

HRID 1515065Notes

Reaction equation

HRID 1515065 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:11]([CH:12]=O)=[CH:10][C:9]=1[Cl:20].[CH3:21][O:22][CH2:23][C:24]([O:26]C)=[O:25].[OH-].[Na+].Cl>C1COCC1.O>[NH2:7][C:8]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:11](/[CH:12]=[C:23](\[O:22][CH3:21])/[C:24]([OH:26])=[O:25])=[CH:10][C:9]=1[Cl:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 80507Methyl methoxyacetateHCID 130204734-Amino-3-chloro-5-(trifluoromethyl)benzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 67043265(Z)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-methoxy-acrylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

26.14 kg (55.91 mol) potassium tert.butoxide solution in THF were metered into a mixture of 10.00 kg (44.73 mol) 4-amino-3-chloro-5-trifluoromethylbenzaldehyde (A), 9.31 kg (89.45 mol) methyl methoxyacetate (B) and 30.0 L tetrahydrofuran and the mixture was stirred for 24 hours at 20° C. Then 7.16 kg (89.45 mol) sodium hydroxide solution (50%) were metered in and the mixture was heated to 30° C. for 1 hour, before 16.31 kg (134.18 mol) hydrochloric acid (30%) and 15.0 L water were added. After the aqueous phase has been separated off, 40 L of the solvent were distilled off and the residue was combined with 25.0 L toluene, before another 40 L solvent were distilled off. The organic phase was combined with 20.0 L water and cooled to 23° C. After the addition of 10.0 L toluene the suspension was stirred for a further 30 minutes, the product was separated off and dried.

Workup

  1. additionwere added
  2. customAfter the aqueous phase has been separated off
  3. distillation40 L of the solvent were distilled off
  4. distillationwere distilled off
  5. temperaturecooled to 23° C
  6. additionAfter the addition of 10.0 L toluene the suspension
  7. stirringwas stirred for a further 30 minutes
  8. customthe product was separated off
  9. customdried

Sources & evidence

ORD record
ord-ffdfd10f6fd447b0801e0314cd197fac
Source dataset
uspto-grants-2012_07
Patent number
US08222402B2

Reaction notes

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