Hydroxypivaldehyde

Hydroxypivaldehyde is the organic compound with the formula HOCH2(CH3)2CCHO. A colorless liquid, it is produced by condensation of formaldehyde and isobutyraldehyde:[2]

CH2O + (CH3)2CHCHO → HOCH2(CH3)2CCHO
Hydroxypivaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.998
EC Number
  • 209-895-4
UNII
  • InChI=1S/C5H10O2/c1-5(2,3-6)4-7/h3,7H,4H2,1-2H3
    Key: JJMOMMLADQPZNY-UHFFFAOYSA-N
  • CC(C)(CO)C=O
Properties
C5H10O2
Molar mass 102.133 g·mol−1
Appearance colorless liquid
Boiling point 141 °C (286 °F; 414 K)
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H319
P264, P280, P305+P351+P338, P337+P313
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The compound is a rare example of a distillable aldol (3-hydroxyaldehyde). Upon standing, it dimerizes reversibly to the dioxane derivative.

Applications

Hydroxypivaldehyde is a precursor to vitamin B5 as is practiced commercially.[3]

Hydroxypivaldehyde is also a precursor to neopentyl glycol by hydrogenation:

HOCH2(CH3)2CCHO + H2 → (CH3)2C(CH2OH)2

References
  1. "3-Hydroxy-2,2-dimethylpropanal". pubchem.ncbi.nlm.nih.gov. Retrieved 31 December 2021.
  2. Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen; Frey, Guido D. (2013). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub3.
  3. Eggersdorfer, Manfred; Laudert, Dietmar; Létinois, Ulla; McClymont, Tom; Medlock, Jonathan; Netscher, Thomas; Bonrath, Werner (2012). "One Hundred Years of Vitamins-A Success Story of the Natural Sciences". Angewandte Chemie International Edition. 51 (52): 12975. doi:10.1002/anie.201205886. PMID 23208776.
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