Water → 1-Acetoxymethylcyclobutanecarboxylic Acid

HRID 728694노트

반응식

HRID 728694 반응식
[OH-:1].[Na+].[OH:3][CH2:4][C:5]1([C:9]([O:11][CH2:12][CH3:13])=O)[CH2:8][CH2:7][CH2:6]1.[OH2:14]>C(O)C>[C:12]([O:11][CH2:9][C:5]1([C:4]([OH:14])=[O:3])[CH2:8][CH2:7][CH2:6]1)(=[O:1])[CH3:13]

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15670506Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

생성물 1

HCID 156705071-Acetoxymethylcyclobutanecarboxylic Acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium hydroxide pellets (1.48 g, 37 mmol) was added to a stirred mixture of ethyl 1-hydroxymethylcyclobutanecarboxylate (4.14 g, 26.1 mmol), water (4 ml) and 95% ethanol (20 ml). The resulting mixture was stirred at room temperature overnight, then concentrated on a rotary evaporator. The residue was treated with toluene (100 ml). Evaporation of this mixture gave a flaky residue which was further dried under high vacuum. The final residue was treated with pyridine (25 ml) and acetic anhydride (15 ml). The resulting mixture was stirred at room temperature for 18 hours, then heated on a steam bath for 20 minutes. It was cooled to room temperature, added crushed ice, then slowly treated with concentrated HCl (12N, 30 ml) with vigorous stirring. It was extracted with a mixture of diethyl ether (120 ml) and methylene chloride (40 ml). The extract was washed with water (4×100 ml), dried, filtered and evaporated to yield the desired product as a yellow oil: NMR (CDCl3) δ=1.82-2.7 (9H, m containing a singlet at 2.076δ), 4.40 (2H, s), 11.46 (H, bs).

후처리

  1. concentrationconcentrated on a rotary evaporator
  2. additionThe residue was treated with toluene (100 ml)
  3. customEvaporation of this mixture
  4. customgave a flaky residue which
  5. customwas further dried under high vacuum
  6. additionThe final residue was treated with pyridine (25 ml) and acetic anhydride (15 ml)
  7. stirringThe resulting mixture was stirred at room temperature for 18 hours
  8. temperatureheated on a steam bath for 20 minutes
  9. temperatureIt was cooled to room temperature
  10. additionadded
  11. customcrushed ice
  12. additionslowly treated with concentrated HCl (12N, 30 ml) with vigorous stirring
  13. extractionIt was extracted with a mixture of diethyl ether (120 ml) and methylene chloride (40 ml)
  14. washThe extract was washed with water (4×100 ml)
  15. customdried
  16. filtrationfiltered
  17. customevaporated

출처 및 근거

ORD 기록
ord-a986234f3fe3479c9eed18b03a5d7299
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05049696

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