Hydrochloric Acid → HCID 59850420, compound

HRID 1922542Notes

Reaction equation

HRID 1922542 reaction equation
[F:1][C:2]([F:25])([F:24])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:23]=[CH:22][C:10]([C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=2)=[O:12])=[CH:9][CH:8]=1.C(O)(=O)[CH2:27][C:28]([OH:30])=[O:29].N1C=CC=CC=1.N1CCCCC1.Cl>>[F:25][C:2]([F:24])([F:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:23]=[CH:22][C:10]([C:11]([O:13][C:14]2[CH:15]=[CH:16][C:17](/[CH:20]=[CH:27]/[C:28]([OH:30])=[O:29])=[CH:18][CH:19]=2)=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 59850427HCID 59850427, compound

Product 1

HCID 59850420HCID 59850420, compoundYield 92.9%

Procedure

5.00 g (14.2 mMol) of 4-formylphenyl 4-(4,4,4-trifluorobutoxy)benzoate and 3.00 g (28.4 mMol) of Malonic acid are dissolved in 18 ml (227.1 mMol) of Pyridin. 1.21 g (14.2 mMol) of Piperidin are added to the suspension which is allowed to react at 100° C. under argon for 1.5 h. The yellow solution is then thrown on ice. The solution is carefully acidified to pH=1-2 with a 25% HCl solution and is stirred for 15 min. The product is filtrated off and dried at room temperature under vacuum for 10 h to give 5.2 g of (2E)-3-(4-{[4-(4,4,4-trifluorobutoxy)benzoyl]oxy}phenyl)acrylic acid as white powder.

Workup

  1. customto react at 100° C. under argon for 1.5 h
  2. filtrationThe product is filtrated off
  3. customdried at room temperature under vacuum for 10 h

Sources & evidence

ORD record
ord-d55b2ec35e714f45a8d4d886e734fe1f
Source dataset
uspto-grants-2012_05
Patent number
US08173749B2

Reaction notes

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