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

HRID 476821

반응식

HRID 476821 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 231054992,2-Dimethyl-3-oxopropyl dodecanoate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d5f20e9a18024ad6b343ccb2f824ffb3
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886618

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