Acetyl chloride → HCID 14654375, compound

HRID 1708865Notes

Reaction equation

HRID 1708865 reaction equation
[Br:1][CH:2]([CH2:6][CH:7]([Br:11])[C:8]([OH:10])=[O:9])[C:3](O)=[O:4].C(Cl)(=O)C>>[Br:1][CH:2]1[CH2:6][CH:7]([Br:11])[C:8](=[O:10])[O:9][C:3]1=[O:4]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 2438732,4-dibromopentanedioic acid

Product 1

HCID 14654375HCID 14654375, compound

Procedure

10.0g (34.5 mmol) of 2,4-dibromoglutaric acid and 4.9 ml (69 mmol) of acetyl chloride are refluxed for a period of 2 hours. Volatiles are removed at 10 torr up to 90° C., and the residue bulb-to-bulb distilled (75°-90° C./0.25 torr), yielding 8.9g (95%) of a colourless, viscous oil. 1H NMR (CDCl3): dl isomer: δ 4.90 (t, 2H, J=6), 2.87 (t, 2H, J=6); meso isomer: 4.77 (dd, 2H, J=6, 10), 3.15 (dt, 1H, J=6 (t), 15 (d)), approx. 2.85 (1H, partially overlapping); dl/meso=5:1. IR (neat): 3007, 2942, 1817, 1775, 1439, 1242, 1109, 1038, 972, 932, 847, 691, 617 cm-1.

Workup

  1. customVolatiles are removed at 10 torr up to 90° C.
  2. distillationthe residue bulb-to-bulb distilled (75°-90° C./0.25 torr)
  3. customyielding 8.9g (95%) of a colourless, viscous oil

Sources & evidence

ORD record
ord-6429c957a4494de7aeec5aa7a26ccdf9
Source dataset
uspto-grants-1990_08
Patent number
US04946839

Reaction notes

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