Water → HCID 53908873, compound

HRID 1731213Notes

Reaction equation

HRID 1731213 reaction equation
CC[O:3][CH2:4][CH3:5].[CH2:6]([OH:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].N1[CH:24]=[CH:23][CH:22]=[CH:21]C=1.O>CCCCC>[CH2:21]1[CH:23]([CH2:24][CH2:5][C:4]([O:18][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:3])[CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 3283Diethyl Ether2×HCID 81931-Dodecanol

Product 1

HCID 53908873HCID 53908873, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To the acid chloride, thus prepared, is added 40 mls. of anhydrous ether and 1.49 g. of 1-dodecanol, followed, at 0°, by 0.8 mls. of pyridine (d20 = 0.982). A white precipitate forms immediately. The mixture is stirred at 24° overnight and then water, ether, and pentane are added to the reaction mixture, the organic layer separated, washed with 3N sulfuric acid, aqueous 15% potassium carbonate, water, and brine, dried over calcium sulfate, and the solvent removed to yield dodecyl 3-cyclopropanepropionate, boiling point 116° at 0.05 mm.

Workup

  1. additionis added 40 mls
  2. customfollowed, at 0°, by 0.8 mls
  3. customthe organic layer separated
  4. washwashed with 3N sulfuric acid, aqueous 15% potassium carbonate, water, and brine
  5. dry with materialdried over calcium sulfate
  6. customthe solvent removed

Sources & evidence

ORD record
ord-ab9d677792cc466f9e80ad8499628d09
Source dataset
uspto-grants-1976_11
Patent number
US03995054

Reaction notes

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