Methanol → HCID 20313170, compound

HRID 839720Notes

Reaction equation

HRID 839720 reaction equation
[C:1]1([CH:7]2[CH2:10][CH:9]([C:11]([OH:13])=[O:12])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14]O>>[C:1]1([CH:7]2[CH2:8][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 47806Cyclobutanecarboxylic acid, 3-phenyl-

Product 1

HCID 20313170HCID 20313170, compound

Procedure

A mixture of the cis and trans isomers of 3-phenylcyclobutane carboxylic acid (6.8g.) in methanol (100ml.) and concentrated suphuric acid (0.5ml.) was refluxed overnight. The solution was concentrated to about 15ml., water was added and the mixture was extracted with ethyl acetate. The ethyl acetate extracts were combined and dried over anhydrous magnesium sulphate, the solvent was evaporated and the residue was distilled, to give methyl 3-phenylcyclobutanecarboxylate as a mixture of cis- and trans-isomers, b.p. 100°-120° C./0.2 mm. Hg.

Workup

  1. concentrationconcentrated suphuric acid (0.5ml.)
  2. temperaturewas refluxed overnight
  3. concentrationThe solution was concentrated to about 15ml
  4. addition, water was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customthe solvent was evaporated
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-16d981d9461048709f30ad42db51dbb8
Source dataset
uspto-grants-1978_06
Patent number
US04096337

Reaction notes

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