Acetyl chloride → HCID 12347356, compound

HRID 1093090Notes

Reaction equation

HRID 1093090 reaction equation
O=C1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[CH:10]([O:15][CH3:16])([O:13][CH3:14])OC.[C:17](Cl)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.CCCCC>[CH3:16][O:15][C:10]1([O:13][CH3:14])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:17])=[O:8])[CH2:3]1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 2277983-Oxocyclopentanecarboxylic acid

Product 1

HCID 12347356HCID 12347356, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8003PentaneSolvent

Procedure

(Tetrahedron, (1977), 33, 1113) A solution of 3-oxocyclopentanecarboxylic acid (10.013 g, 78 mmol) and trimethyl orthoformate (60.5 mL, 547 mmol) in MeOH (120 mL) was treated with acetyl chloride (7.78 mL, 109 mmol) and stirred under a nitrogen atmosphere for 5 days. The reaction solution was poured into a stirred suspension of anhydrous sodium carbonate (32 g) in pentane (250 mL) and stirred for 3 hrs. The solids were removed by filtration (2×) and concentrated under reduced pressure to give the target compound (15.4 g, 82 mmol, 105% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.67 (3 H, s), 3.20 (3 H, s), 3.18 (3 H, s), 2.82-2.93 (1 H, m), 2.01-2.15 (2 H, m), 1.77-2.01 (4 H, m).

Workup

  1. stirringstirred for 3 hrs
  2. customThe solids were removed by filtration (2×)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2dfbfa1eb2d648118ef2c3a2954e9e9a
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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