Toluene → 2,2-Dimethyl-3-oxopropyl dodecanoate

HRID 476821Notes

Reaction equation

HRID 476821 reaction equation
[C:1]([OH:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:15][C:16]([CH:20]=O)([CH2:18][OH:19])[CH3:17].C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:1]([O:14][CH2:15][C:16]([CH3:20])([CH3:17])[CH:18]=[O:19])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 3893Lauric AcidHCID 116993-Hydroxy-2,2-dimethylpropionaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 231054992,2-Dimethyl-3-oxopropyl dodecanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a hot (80° C.) solution of lauric acid (70 g., 0.35 mole), and hydroxypivaldehyde (30.6 g., 0.3 mole) in 120 g. of toluene was added 1.75 g. of p-toluenesulfonic acid monohydrate (0.009 mole). The mixture was then heated at total reflux for 1.5 hrs. and water generated in the reaction mixture was removed by azeotropic distillation. The reaction mixture was cooled, washed with saturated aqueous sodium bicarbonate and brine, then dried over magnesium sulfate, filtered, and evaporated in vacuo. GLC analysis of the product showed that it contained 90% of the desired laurate ester. Fractional distillation of the crude sample gave a product cut, b.p. 180° C./4.0 mm, of 95% purity (GLC, area %). NMR (CDCL3): 9.73 (s, 1H,--CHO), 4.2 (s, 2H, --CO2CH2 --), 2.3 (t, 2H, --CH2CO2 --), 0.9-1.9 (m, 23H, CH2 (CH2)10CH2CO 2 --), and 1.17 (s, 6H, --C(CH2)2.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat total reflux for 1.5 hrs
  3. customwas removed by azeotropic distillation
  4. temperatureThe reaction mixture was cooled
  5. washwashed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. distillationFractional distillation of the crude sample
  10. customgave a product cut, b.p. 180° C./4.0 mm

Sources & evidence

ORD record
ord-d5f20e9a18024ad6b343ccb2f824ffb3
Source dataset
uspto-grants-1989_12
Patent number
US04886618

Reaction notes

Loading…