Malonic Acid → 2-Chloro-4-(2-tetrahydropyranyloxy)cinnamic acid

HRID 2225539Notes

Reaction equation

HRID 2225539 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.ClC1C=C(O)C=CC=1C=O.C(O)(=O)[CH2:28][C:29]([OH:31])=[O:30].N1CCCCC1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:28][C:29]([OH:31])=[O:30]

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 8082PiperidineHCID 1853632-Chloro-4-hydroxybenzaldehydeHCID 221373212-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

Product 1

HCID 545381342-Chloro-4-(2-tetrahydropyranyloxy)cinnamic acidYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using 4.8 g of 2-chloro-4-(2-tetrahydropyranyloxy)benzaldehyde derived from 2-chloro-4-hydroxybenzaldehyde by the introduction of tetrahydropyranyl group thereinto, 4.2 g of malonic acid, 80 ml of pyridine, and 0.5 ml of piperidine, a reaction similar to that performed in Example 99 was carried out. As a result, 3.1 g of 2-chloro-4-(2-tetrahydropyranyloxy)cinnamic acid was obtained as crystal, which had the following physiochemical properties:

Sources & evidence

ORD record
ord-3a7632feda264ccd8d81f8fbab9a9634
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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