HCID 522993, compound → Methyl 5-Hydroxy-2,2,4,4-tetramethyl-3-ketovalerate

HRID 1722513Notes

Reaction equation

HRID 1722513 reaction equation
[CH3:1][C:2]([CH3:12])([C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])[C:3]([O:5][CH3:6])=[O:4].[CH3:13][O-:14].[Na+]>CO>[OH:14][CH2:13][C:8]([CH3:10])([CH3:9])[C:7](=[O:11])[C:2]([CH3:1])([CH3:12])[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 522993HCID 522993, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 14723651Methyl 5-Hydroxy-2,2,4,4-tetramethyl-3-ketovalerate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 172 g. (1.0 mole) methyl 2,2,4-trimethyl-3-ketovalerate, 5.4 g. (0.10 mole) sodium methoxide and 33 g. (0.36 mole) paraformalde in 250 ml. methanol is heated at reflux for eight hours. The mixture is quenched by addition of water, neutralized with hydrochloric acid, extracted with ethyl ether, washed with water, brine and solvent evaporated. The residue is purified by vacuum distillation or chromatography on silica gel to provide the purified product.

Workup

  1. additionA mixture of 172 g
  2. temperatureat reflux for eight hours
  3. customThe mixture is quenched by addition of water
  4. extractionextracted with ethyl ether
  5. washwashed with water, brine and solvent
  6. customevaporated
  7. distillationThe residue is purified by vacuum distillation or chromatography on silica gel
  8. customto provide the purified product

Sources & evidence

ORD record
ord-e3a7e890b2e0474a8c246dcca4c0b573
Source dataset
uspto-grants-1989_08
Patent number
US04855454

Reaction notes

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