Acetyl chloride → Acetoacetic Acid

HRID 1077236

Reaction equation

HRID 1077236 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:22]#[CH:23])[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2].C([O:27][C:28](=[O:30])[CH3:29])(=O)C.[C:31](Cl)(=[O:33])[CH3:32]>N1C=CC=CC=1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17](=[CH:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:22]#[CH:23])[OH:21])[CH:16]=[C:15]([OH:20])[CH2:14][CH2:13]4)[CH3:2].[CH3:32][C:31]([CH2:29][C:28]([OH:27])=[O:30])=[O:33]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 13109Levonorgestrel

Product 2

HCID 96Acetoacetic AcidHCID 8673349013-Ethyl-17alpha-ethynyl-3,17-dihydroxygona-3,5-diene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Reflux dl-13-ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-one (1.0 g) for one and one-half hours with acetic anhydride (16 cc), acetyl chloride (8.0 cc) and pyridine (0.8 cc). Remove the liquids under reduced pressure and partition the dry crystalline residue between benzene-ether and water. Wash the organic solvents under reduced pressure and triturate the residue with ice-cold ether to provide dl-13-ethyl-17α-ethynyl-3,17-dihydroxygona-3,5-diene, diacetate (0.725 g) m.p. 144°-150°C; λ max. KBr. 3.09, 5.67, 5.77 μ; λ max. EtOH 236 mμ (ε19,300).

Workup

  1. customRemove the liquids under reduced pressure
  2. custompartition the dry crystalline residue between benzene-ether and water
  3. washWash the organic solvents under reduced pressure
  4. customtriturate the residue with ice-cold ether

Sources & evidence

ORD record
ord-970a98dc86604ab49a7bc052e6e13fe3
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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