Methanol → HCID 20313170, compound

HRID 2420137Notes

Reaction equation

HRID 2420137 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>S(=O)(=O)(O)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

4

Reactant 2

HCID 887MethanolHCID 47806Cyclobutanecarboxylic acid, 3-phenyl-

Product 1

HCID 20313170HCID 20313170, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of the cis and trans isomers of 3-phenylcyclobutane carboxylic acid (6.8g.) in methanol (100ml.) and concentrated sulphuric 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. temperaturewas refluxed overnight
  2. concentrationThe solution was concentrated to about 15ml
  3. addition, water was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customthe solvent was evaporated
  7. distillationthe residue was distilled

Sources & evidence

ORD record
ord-949c62a2f5b74c00a80643ac9bc9881e
Source dataset
uspto-grants-1978_08
Patent number
US04109015

Reaction notes

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