Sodium Iodide → HCID 86730618, compound

HRID 1428913Notes

Reaction equation

HRID 1428913 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([I:12])[C:9]([O:13][CH3:14])=[CH:8][C:5]=1[CH:6]=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CS(Cl)(=O)=O.[I-].[Na+].[P:28]([O:35]CC)([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([I:12])[C:9]([O:13][CH3:14])=[CH:8][C:5]=1[CH2:6][P:28](=[O:35])([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])[CH3:2]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 31215Triethyl phosphiteHCID 31297Methanesulfonyl chlorideHCID 21226445Aluminium lithium hydrideHCID 86730619HCID 86730619, compound

Product 1

HCID 86730618HCID 86730618, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydroquinone can be added to a solution of sodium hydride (NaH) dissolved in tetrahydrofuran (THF) and combined with methyl bromide yielding para-methoxyphenol. The para-methoxyphenol can be extracted and added to a solution of tosyl chloride (TsCl) dissolved in pyridine and tetrahydrofuran (THF) at room temperature, yielding para-methoxytosyloxybenzene. The para-methoxytosyloxybenzene can be extracted and added to a solution of diatomic iodine (I2) and potassium iodide trioxide (KIO3) dissolved in sulfuric acid (H2SO4) and acetic acid (CH3COOH) yielding 4-methoxy-3-iodo-1-tosyloxybenzene. The 4-methoxy-3-iodo-1-tosyloxybenzene can be extracted and added to a solution of aqueous sodium hydroxide (NaOH) and tert-butanol, removing the tosylate protecting group and yielding 4-methoxy-3-iodophenol. The 4-methoxy-3-iodophenol can be extracted and exposed to resin-bound triphenyphosphine (PPh3) in a solution of azopyridine and ethanol (CH3CH2OH) in a salt bath at 0° C., yielding 4-ethoxy-2-iodomethoxybenzene. The 4-ethoxy-2-iodomethoxybenzene can be extracted and added to a solution of titanium tetrachloride (TiCl4) and 1,1-dichlorodimethylether (CHCl2OCH3) dissolved in dichloromethane (CH2Cl2) in a salt bath at −10° C., yielding 2-ethoxy-4-iodo-5-methoxybenzaldehyde. The 2-ethoxy-4-iodo-5-methoxybenzaldehyde can be added to lithium aluminum hydride (LiAlH4) and methanesulfonyl chloride (CH3SO2Cl) dissolved in pyridine, and then sodium iodide (NaI) and triethyl phosphite (P(OCH2CH3)3) can be added to the reaction mixture, yielding diethyl 2-ethoxy-4-iodo-5-methoxybenzylphosphonate.

Sources & evidence

ORD record
ord-3ff046e5c19e4d85bc362374539b2b80
Source dataset
uspto-grants-2015_01
Patent number
US08937148B2

Reaction notes

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