Acetyl chloride → HCID 11429511, compound

HRID 1951975Notes

Reaction equation

HRID 1951975 reaction equation
[CH3:1][O:2][CH:3](OC)[C:4]([O:6][CH3:7])=[O:5].C([Cl:13])(=O)C.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>II>[Cl-:13].[CH3:1][O:2][CH:3]([P+:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11776TriphenylphosphineHCID 66647Acetic acid, 2,2-dimethoxy-, methyl ester

Product 1

HCID 11429511HCID 11429511, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 807IodineCatalyst

Conditions

Temperature
55 °C

Procedure

25 g (186 mmol) of methyl dimethoxyacetate is added to 27 ml (215 mmol) of acetyl chloride at room temperature. 0.1 g (0.2% molar) of iodine is added and then the reaction mixture is stirred at 55° C. for 16 hours. The excess of acetyl chloride is evaporated under vacuum, then the residue is dissolved in 100 ml of dichloromethane. 49 g (204 mmol) of triphenylphosphine is added and then the reaction mixture is stirred at 37° C. for 3 hours. The solvents are evaporated and the residue is crystallized in diisopropyl ether. 70 g (88%) of (methoxy-methoxycarbonyl-methyl)-triphenyl-phosphonium chloride is obtained.

Workup

  1. customThe excess of acetyl chloride is evaporated under vacuum
  2. dissolutionthe residue is dissolved in 100 ml of dichloromethane
  3. stirringthe reaction mixture is stirred at 37° C. for 3 hours
  4. customThe solvents are evaporated
  5. customthe residue is crystallized in diisopropyl ether

Sources & evidence

ORD record
ord-60f60fc882b64f879e47448bf4b856fe
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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