Formaldehyde → HCID 21510427, compound

HRID 1576955Notes

Reaction equation

HRID 1576955 reaction equation
[O:1]([CH2:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]=[O:16].[OH-].[Na+]>C(O)C>[OH:16][CH2:15][CH:8]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 1816272-Butanone, 3,3-dimethyl-1-phenoxy-

Product 1

HCID 21510427HCID 21510427, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1Phenoxy-3,3-dimethyl-butan-2-one (192.2 g, 1.0 mol) prepared according to German Offenlegungsschrift, i.e., (German Published Specification No. 2,105,490; Example 3) and having a boiling point of 75°-83°C at 0.08 atmospheres is dissolved in ethanol (800 ml) and a 30% formaldehyde solution (240 ml, 2.4 mols) is added. A 10% sodium hydroxide solution (5 ml) is then added until the pH is 9. The reaction mixture is heated for 4 hours reflux and the solvent is distilled off in vacuo. The resulting precipitate is filtered off, well rinsed with petroleum ether and discarded. The filtrate is freed from the solvent in vacuo and the resulting oil is taken up in ether and extracted by shaking with water. The organic phase is dried over sodium sulphate and freed from the solvent and the residue is purified by vaccum distillation to afford 145 g (65% of theory) of 1 -hydroxy-2-phenoxy-4,4-dimethyl-pentan-3-one, boiling point 95°-100°C (0.1 mm Hg).

Workup

  1. temperatureThe reaction mixture is heated for 4 hours
  2. temperaturereflux
  3. distillationthe solvent is distilled off in vacuo
  4. filtrationThe resulting precipitate is filtered off
  5. washwell rinsed with petroleum ether
  6. extractionextracted
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. distillationthe residue is purified by vaccum distillation

Sources & evidence

ORD record
ord-323fee016515449dab10900b1fec6ca0
Source dataset
uspto-grants-1976_09
Patent number
US03983240

Reaction notes

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