Hydrochloric Acid → Succinic Acid Monohex-3-enyl Ester

HRID 2304961Notes

Reaction equation

HRID 2304961 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH2:8]([OH:14])[CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH3:13].N1C=CC=CC=1.Cl>ClCCl.CN(C1C=CC=CN=1)C.CCOCC>[CH2:8]([O:14][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])[CH2:9][CH:10]=[CH:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7922Succinic anhydrideHCID 52811673-Hexenol

Product 1

HCID 86586591Succinic Acid Monohex-3-enyl EsterYield 92.5%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 100 g succinic anhydride, 100 g cis-3-hexen-1-ol, 88.5 ml pyridine and 7.3 g dimethylaminopyridine in 500 ml dichloromethane was refluxed for 4 hours. Ether was added and the mixture was acidified with HCl 2N then washed with brine. The organic layer was dried over magnesium sulfate and concentrated. The residue was distilled under vacuum to afford 185 g of product.

Workup

  1. temperaturewas refluxed for 4 hours
  2. washthen washed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-e3e39f96d5b94d9e846a89f493a7d16f
Source dataset
uspto-grants-2002_08
Patent number
US06437150B1

Reaction notes

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