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Chemical Structure| 38169-97-0 Chemical Structure| 38169-97-0

Structure of 38169-97-0

Chemical Structure| 38169-97-0

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Product Details of [ 38169-97-0 ]

CAS No. :38169-97-0
Formula : C7H5IO2
M.W : 248.02
SMILES Code : O=CC1=C(I)C=CC=C1O
MDL No. :MFCD15143223
InChI Key :OMXBWJYYNNGFIV-UHFFFAOYSA-N
Pubchem ID :12023200

Safety of [ 38169-97-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P261-P280-P305+P351+P338-P304+P340-P405

Application In Synthesis of [ 38169-97-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 38169-97-0 ]

[ 38169-97-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 50-00-0 ]
  • [ 626-02-8 ]
  • [ 38169-97-0 ]
  • [ 38170-02-4 ]
YieldReaction ConditionsOperation in experiment
The reaction was carried out in a large flask equipped with a stirrer and reflux condenser. A solution of 3-Iodophenol (1Og; 45,4 mmol) in acetonitrile (160 ml) was cooled in an ice-water bath and magnesium chloride (12.8g; 134.4 mmol) was added to the phenol in small batches over 10 minutes to give a pink cloudy solution. Triethylamine (50.6 ml; 363.2 mmol) was added to the acetonitrile solution gradually over 5 minutes keeping the solution at ~0 0C and this was followed with the addition of paraformaldehyde (19.2g; 636 mmol) in small 0.5-lg batches over 10 minutes. Once the addition of the paraformaldehyde was complete the reaction vessel with the reflux condenser in place was removed from the cooling bath and warmed quickly to 80 0C (bath temperature). After 0.25 h of heating the solids started to dissolve and around 1 h of heating the reaction solution was almost a homogeneous golden yellow color which slowly started to turn to an orange color. The reaction was kept at 80 0C for 18.5 hours; the reaction had become a deep orange in color. The reaction mixture was cooled to room temperature and quenched with saturated aqueous ammonium chloride solution (350 ml). The aqueous acetonitrile mixture was shaken with EtOAc (150 ml) and transferred into a separatory funnel. The layers were separated and the aqueous layer extracted with EtOAc (2 x 150 ml). The three EtOAc layers were combined and washed successively with saturated aqueous NaHCO3 (2 x 150 ml), IN hydrochloric acid (2 x 150 ml) and lastly with saturated brine (2 x 100 ml). The orange colored solution with the crude product was dried over anhydrous Na2SO4 powder, filtered through a Celite pad and the filtrate concentrated under reduced pressure to leave an orange colored oil that slowly solidified on standing. The solid was purified in 3 batches on a Biotage SPl system on 4OM Flash silica cartridge using a gradient of EtOAc and hexanes 0->2% (350 ml), 2->15% (1250 ml) 15->20% (350 ml). The aldehyde fractions were concentrated down to leave an off-white feathery solid. This solid was crystallized from hexanes to give 6g of the pure aldehyde. The mother liqours were purified on silica gel preparative tic plates eluted with EtOAc and hexanes (7:93 v/v) from which a further 300 of the desired aldehyde was recovered (Total 6.3g). There was also -800 mg of the isomeric aldehyde obtained from the purification. The NMR data for 2-hydroxy-4-iodobenzaldehyde is as follows :- 1H-NMR (400 MHz, CDCl3) delta: 7.25 (d, J = 8 Hz, IHO, 7.42 (dd, J = 8 & 1.5 Hz, IH), 7.46 (d, J - 1.5Hz, IH), 9.87 (s, IH)5 11.04 (s, IH).The NMR data for the isomeric 2-hydroxy-6-iodobenzaldehyde was:- 1H-NMR (400 MHz, CDCl3) delta: 6.99 (d, J = 8 Hz, IH), 7.15 (t, J = 8 Hz, IH)3 7.50 (d, J = 8 Hz, IH), 10.09 (s, IH), 12.07 (s, IH).
 

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Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Halogenation of Phenols • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reformatsky Reaction • Reimer-Tiemann Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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