Potassium Carbonate → 5-Chloro-2-[4-(2-hydroxy-ethoxy)-phenoxy]-benzaldehyde

HRID 1095111Notes

Reaction equation

HRID 1095111 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].C([Si](C)(C)[O:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][C:23]2[CH:22]=[CH:21][C:20]([O:19][CH2:18][CH2:17][OH:16])=[CH:25][CH:24]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27735865-Chloro-2-fluorobenzaldehydeHCID 220333784-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenol

Product 1

HCID 577434215-Chloro-2-[4-(2-hydroxy-ethoxy)-phenoxy]-benzaldehydeYield 75.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In a manner similar to the method described in Example 50a, 5-chloro-2-fluorobenzaldehyde (1.2 g, 7.6 mmol) (Aldrich) was reacted with 4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenol (2.1 g, 7.8 mmol) prepared in Example 60b and K2CO3 in N,N-dimethylacetamide at 170° C. for 0.5 h to give 5-chloro-2-[4-(2-hydroxy-ethoxy)-phenoxy]-benzaldehyde as a colorless oil (Yield 1.68 g, 75%).

Sources & evidence

ORD record
ord-f5dbe5546a7e4a5e88e86dd6d3e801ad
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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