Hydrochloric Acid → HCID 57264371, compound

HRID 486323Notes

Reaction equation

CCOCC.Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].[CH2:17]([OH:20])[C:18]#[CH:19].Cl>[OH-].[Na+]>[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:20][CH2:17][C:18]#[CH:19])([OH:16])=[O:15]

Participants

Conditions

Temperature: 60 °C

Procedure

An ether solution of 8-bromooctanoic acid (15.1 g, 65 mmol) was reacted with 325 mmol propargyl alcohol dissolved in aqueous NaOH solution containing 975 mmol NaOH. After heating at 60° C. for 24 hours, the reaction was stopped by neutralizing the base with hydrochloric acid. Ether extraction provided 16 g of opaque white liquid, which was further purified by distillation under reduced pressure (160°-163° C./0.075 mm Hg). The sample was analyzed with 1H-NMR in CDCl3, and the observed chemical shift peaks were at δ=1.34 (br singlet, 6H, --(CH2)--), 1.61 (pentate center, 4H, --(CH2)--), 2.35 (t, 2H, CH2 --COO), 2.42, (d, J=2.6 Hz, 1H, C≡CH), 3.51 (t, J=6.6 Hz, 2H, --CH2 --O), and 4.14 (d, J=2.6 Hz, 2H, O--CH2 --C≡C). Observed IR (KBr) peaks were at 1709 (COOH), 2120 (--C≡C--) and 3298 (--C≡CH) cm-1.

Workup

extractionEther extraction

Sources & evidence

ORD record: ord-1aa13a1a8c4149c9a2d9c7743014c18f
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290960

Reaction notes

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