Iodine chloride → 3-Iodo-3-phenylprop-2-en-1-ol

HRID 1063416Notes

Reaction equation

COCCO[AlH2-]OCCOC.[Na+].[C:13]1([C:19]#[C:20][CH2:21][OH:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[I:23]Cl.C(O)(=O)C(C(C(O)=O)O)O.[Na].[K]>C1(C)C=CC=CC=1.C(OCC)C>[I:23][C:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:20][CH2:21][OH:22]

Participants

Conditions

Temperature: -78 °C

Procedure

Red-Al™ (3.4M in toluene, 33 ml) was dissolved in diethyl ether (100 ml) and cooled to −10° C. to which 3-phenyl-2-propyn-1-ol (10 g, 0.076 mol) dissolved in diethyl ether (10 ml) was added dropwise, causing the solution to turn a dark red/brown colour. The reaction was stirred for 1 hour. The solution was cooled to −78° C. and iodine monochloride (1.0M solution in dichloromethane, 114 ml) was added causing the solution to turn a dark brown colour. The mixture was allowed to warm to room temperature and stirred for 1 hour. A 10% solution of potassium sodium tartaric acid (800 ml) was added, producing a white precipitate, this was removed by filtration and the filtrate was extracted with diethyl ether (3×75 ml). The combined organic extracts were washed with sodium thiosulphate (5×60 ml), brine, dried (MgSO4) and the solvent removed in vacuo to afford the crude title compound as a light brown oil (19.5 g, 95%).

Workup

additionwas added dropwise
temperatureto warm to room temperature
stirringstirred for 1 hour
customproducing a white precipitate
customthis was removed by filtration
extractionthe filtrate was extracted with diethyl ether (3×75 ml)
washThe combined organic extracts were washed with sodium thiosulphate (5×60 ml), brine
dry with materialdried (MgSO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-5160708203a244d998f82e2a5938aa12
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06964981B2

Reaction notes

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