Sodium Hydroxide → HCID 54002484, compound

HRID 345505

Reaction equation

HRID 345505 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.S(Cl)([Cl:19])(=O)=O.[OH-].[Na+]>C(Cl)Cl.CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH:5]([Cl:19])[C:6](=[O:14])[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 288215Methyl 4-(4-methylphenyl)-4-oxobutanoate

Product 1

HCID 54002484HCID 54002484, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of 152.6 g (0.74 mole) of 3-(4-methylbenzoyl)propionic methyl ester in 225 mL of methylene chloride was cooled to -5° C. in methanol:ice bath. A solution of 109.9 g (66 mL, 0.81 mole) of sulfuryl chloride (97%) in 65 mL of methylene chloride was added dropwise at a rate which maintained the temperature at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was cooled to 0° C. in an ice bath and treated with 3N sodium hydroxide until just basic. The organic portion was separated, dried over magnesium sulfate and concentrated in vacuo (172.9 g). The oil was distilled at 125° C. (150 mm Hg) in 4 fractions. A sample of fraction 2 was sent for elemental analysis.

Workup

  1. temperatureto warm to ambient temperature
  2. temperatureThe reaction mixture was cooled to 0° C. in an ice bath
  3. customThe organic portion was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo (172.9 g)
  6. distillationThe oil was distilled at 125° C. (150 mm Hg) in 4 fractions

Sources & evidence

ORD record
ord-10f3278064f54a2e88bfce922bcbc51e
Source dataset
uspto-grants-1991_10
Patent number
US05057534

Linked notes

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