Water → 1-Acetoxymethylcyclobutanecarboxylic Acid

HRID 231606Notes

Reaction equation

HRID 231606 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 156705071-Acetoxymethylcyclobutanecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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 roatry evaporator. The residue was treated with toluene (100 ml). Evaporation of this mixture gave a flaky resiude 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 hour, 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 2.07δ), 4.40 (2H, s), 11.46 (H, bs).

Workup

  1. concentrationconcentrated on a roatry evaporator
  2. additionThe residue was treated with toluene (100 ml)
  3. customEvaporation of this mixture
  4. customgave a flaky resiude 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 hour
  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

Sources & evidence

ORD record
ord-a66db22d9b9e4557b3f549f277a8a227
Source dataset
uspto-grants-1989_07
Patent number
US04847306

Reaction notes

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