Neopentyl glycol → 2-Carboxy-5,5-dimethyl-1,3-dioxane

HRID 2075280노트

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HRID 2075280 반응식
O.[C:2]([OH:6])(=[O:5])[CH:3]=[O:4].[CH3:7][C:8]([CH3:13])([CH2:11]O)[CH2:9][OH:10]>C1C=CC=CC=1>[C:2]([CH:3]1[O:10][CH2:9][C:8]([CH3:13])([CH3:11])[CH2:7][O:4]1)([OH:6])=[O:5]

참가 물질

4

반응물 2

HCID 31344Neopentyl glycolHCID 15620607Glyoxylic acid, monohydrate

생성물 1

HCID 114351012-Carboxy-5,5-dimethyl-1,3-dioxane수율 73.4%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Following a general procedure,23 a mixture of glyoxylic acid monohydrate (5.0 g, 54 mmol), 2,2-dimethyl 1,3-propanediol (8.5 g, 81 mmol) and Amberlyst-15 ion-exchange resin (100 mg) in benzene (140 mL) was refluxed for 15 h in a flask fitted with a Dean-Stark apparatus. The reaction mixture was filtered. The filtrate was concentrated and then refluxed with 20% aqueous NaOH (50 mL) for 30 min. The resulting alkaline solution was extracted with ether and neutralized in the cold with dilute HCl. At the end the pH was brought to 1.0 using H3PO4. The acidified aqueous layer was extracted with ether. The extracts were combined, dried (Na2SO4) and concentrated to afford a white solid (6.349 g, 73%): mp 58-60° C.; 1H NMR δ 0.80 (s, 3H), 1.22 (s, 3H), 3.57 (d, J=12.0 Hz, 2H), 3.79 (d, J=12.0 Hz, 2H), 4.97 (s, 1H); 13C NMR δ 169.1, 124.7, 95.8, 77.5, 30.6, 23.0, 21.9; FAB-MS obsd 161.0806, calcd 161.0814 (C7H12O4).

후처리

  1. temperaturewas refluxed for 15 h in a flask
  2. customfitted with a Dean-Stark apparatus
  3. filtrationThe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated
  5. temperaturerefluxed with 20% aqueous NaOH (50 mL) for 30 min
  6. extractionThe resulting alkaline solution was extracted with ether
  7. extractionThe acidified aqueous layer was extracted with ether
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7b57ed40e68d4a779a26c27919e7ba0e
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919615B2

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