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Water → 2-[(4-Carboxyphenyl)methylene]-1,3-dicyclopropyl-1,3-propanedione

HRID 2081728
Notes
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Reaction equation

HRID 2081728 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH:12]1([C:15](=[O:22])[CH2:16][C:17]([CH:19]2[CH2:21][CH2:20]2)=[O:18])[CH2:14][CH2:13]1.O>FC(F)(F)C(O)=O>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:16]([C:15]([CH:12]2[CH2:14][CH2:13]2)=[O:22])[C:17]([CH:19]2[CH2:21][CH2:20]2)=[O:18])=[CH:6][CH:5]=1)([OH:3])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 120884-Formylbenzoic acidHCID 137807821,3-Dicyclopropylpropane-1,3-dione

Product 1

HCID 190963932-[(4-Carboxyphenyl)methylene]-1,3-dicyclopropyl-1,3-propanedione

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

The procedure described in Example 19 was repeated by using 3.0 g 4-carboxybenzaldehyde and 3.06 g 1,3-dicyclopropyl-1,3-propanedione. Yield 1.7 g, mp 175°-178° C. in trifluoroacetic acid (10 ml) thionylchloride (4 ml) and catalytic amount of water (0,05 ml) were added at room temperature. The solution was stirred over right at 20° C. The solvent was evaporated and the residue was destilled in vacuo, bp 110° C./1,5 mbar. Yield 5,3 g (41%).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d74341ceb52a4b2b9bfe3bc7fdeae916
Source dataset
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05185370

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes