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

HRID 476821

反応式

HRID 476821 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 231054992,2-Dimethyl-3-oxopropyl dodecanoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5f20e9a18024ad6b343ccb2f824ffb3
出典データセット
uspto-grants-1989_12
特許番号
US04886618

関連ノート

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