Butyric Acid → HCID 15135436, compound

HRID 1589940Notes

Reaction equation

HRID 1589940 reaction equation
[C:1]([OH:6])(=[O:5])[CH2:2][CH2:3][CH3:4].[C:7](=[O:15])([O:12][CH2:13][CH3:14])[O:8][CH:9](Cl)[CH3:10].[OH-].[K+]>C(#N)C.O.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[C:7](=[O:15])([O:12][CH2:13][CH3:14])[O:8][CH:9]([O:5][C:1](=[O:6])[CH2:2][CH2:3][CH3:4])[CH3:10]

Participants

7

Reactant 3

HCID 264Butyric AcidHCID 14797Potassium HydroxideHCID 162095Carbonic acid, 1-chloroethyl ethyl ester

Product 1

HCID 15135436HCID 15135436, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 66854Benzyltrimethylammonium hydroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of butyric acid (0.58 g., 6.55 mmol.) and 1-chloroethyl ethyl carbonate (1 g., 6.55 mmol.) in acetonitrile (15 ml.) is added water (2 drops), benzyltrimethylammonium hydroxide (2 drops of 40% aqueous solution) and potassium hydroxide (0.44 g., 7.86 mmol.). The reaction mixture is stirred under reflux for 4 hours, it is filtered, and ether is added to the filtrate. The combined organic phase is thrice washed with water, dried over magnesium sulfate and filtered. The filtrate is concentrated in vacuo and the residue is distilled at 75° C. in a Kugelrohr apparatus at 0.1 mm. Hg. Yield 0.57 g. (42.7%). VPC chromatography on a 4 m, 20% Carbowax 20M on Chromosorb WAW, temperature 110° C., flow rate 65 ml./min., gave a retention time of 66.6 minutes. 1H-NMR ppm (CDCl3): 6.77 (q. J=5 Hz, 1H), 4.22 (q. J= 7 Hz, 2H), 2.32 (t, J=7.5 Hz, 2H), 1.66 (sextet, J=7.5 Hz, 2H), 1.52 (d, J=5.5 Hz. 3H), 1.318 (t, J=7.5 Hz, 3H). 0.95 (t. J=7.5 Hz, 3H).

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationit is filtered
  3. additionether is added to the filtrate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo
  8. distillationthe residue is distilled at 75° C. in a Kugelrohr apparatus at 0.1 mm. Hg
  9. customon Chromosorb WAW, temperature 110° C., flow rate 65 ml
  10. custom, gave a retention time of 66.6 minutes

Sources & evidence

ORD record
ord-940c2916946a40049ce75249305bba05
Source dataset
uspto-grants-1993_04
Patent number
US05200553

Reaction notes

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