Potassium Carbonate → 5-Chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-benzaldehyde

HRID 1095141Notes

Reaction equation

HRID 1095141 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[O:11]1[C:15]2([CH2:20][CH2:19][CH:18](OS(C)(=O)=O)[CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:18]2[CH2:19][CH2:20][C:15]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:16][CH2:17]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Product 1

HCID 577432965-Chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-benzaldehydeYield 34.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in example 4a, 5-chlorosalicylaldehyde (2.32 g, 14.8 mmol) (Aldrich) reacted with methanesulfonic acid 1,4-dioxa-spiro[4.5]dec-8-yl ester (3.5 g, 14.8 mmol) and K2CO3 in N,N-dimethylformamide to give 5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-benzaldehyde as a colorless oil (Yield 1.5 g, 34%).

Sources & evidence

ORD record
ord-584440eaf1a4429f9d1a0802a5d18384
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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