2-Hydroxy-5-methoxybenzaldehyde
{{short description|Organic compound and isomer of vanillin}}
{{Chembox
| verifiedrevid = 401764526
| ImageFile = 2-Hydroxy-5-methoxybenzaldehyde.svg
| ImageSize = 160
| ImageAlt1 = 2-Hydroxy-5-methoxybenzaldehyde molecule
| PIN = 2-Hydroxy-5-methoxybenzaldehyde
| OtherNames = 5-Methoxysalicylaldehyde; 2-Formyl-4-methoxyphenol; 6-Hydroxy-m-anisaldehyde
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21168855
| InChIKey = AFUKNJHPZAVHGQ-UHFFFAOYAN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H10O3/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-6H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FZHSPPYCNDYIKD-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 672-13-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = GYT2Q9UR3W
| EINECS = 211-589-0
| PubChem = 24848799
| SMILES = COC1=CC(=C(C=C1)O)C=O
| InChI = InChI=1S/C8H8O3/c1-11-7-2-3-8(10)6(4-7)5-9/h2-5,10H,1H3
}}
| Section2 = {{Chembox Properties
| Formula = | C=8 | H=8 | O=3
| Appearance = Yellow to yellow-green liquid
| Density = 1.219 g/mL
| MeltingPtC = 4
| BoilingPtC = 250
| Solubility =
| RefractIndex = 1.578
}}
}}
2-Hydroxy-5-methoxybenzaldehyde is an organic compound and an isomer of vanillin.
Synthesis and reactions
The chemical is produced by the Reimer-Tiemann reaction on 4-methoxyphenol with a 79% yield.{{cite book|last1=Wynberg|first1=Hans|last2=Meijer|first2=Egbert W.|title=The Reimer–Tiemann Reaction|year=2005|page=16|doi=10.1002/0471264180.or028.01|isbn=9780471264187}}
It reacts with malononitrile to form 2-imino-6-methoxy-2H-1-benzopyran-3-carbonitrile.{{cite journal|last1=Dinparast|first1=Leila|last2=Hemmati|first2=Salar|last3=Zengin|first3=Gokhan|last4=Alizadeh|first4=Ali Akbar|last5=Bahadori|first5=Mir Babak|last6=Kafil|first6=Hossein Samadi|last7=Dastmalchi|first7=Siavoush|title=Rapid, Efficient, and Green Synthesis of Coumarin Derivatives via Knoevenagel Condensation and Investigating Their Biological Effects|journal=ChemistrySelect|volume=4|issue=31|year=2019|pages=9211–9215|issn=2365-6549|doi=10.1002/slct.201901921|s2cid=202077668 }} It can be reduced by sodium borohydride in ethanol to form 2-hydroxy-5-methoxybenzyl alcohol.{{cite journal|last1=Cheng|first1=Yan|last2=Ono|first2=Masahiro|last3=Kimura|first3=Hiroyuki|last4=Kagawa|first4=Shinya|last5=Nishii|first5=Ryuichi|last6=Kawashima|first6=Hidekazu|last7=Saji|first7=Hideo|title=Fluorinated Benzofuran Derivatives for PET Imaging of β-Amyloid Plaques in Alzheimer's Disease Brains|journal=ACS Medicinal Chemistry Letters|volume=1|issue=7|year=2010|pages=321–325|issn=1948-5875|doi=10.1021/ml100082x|pmid=24900214 |pmc=4007906}}
See also
References
{{reflist}}
{{DEFAULTSORT:Hydroxy-5-methoxybenzaldehyde, 2-}}
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