Methanol → HCID 54520137, compound

HRID 1415327Notes

Reaction equation

HRID 1415327 reaction equation
[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]3[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[C:11]=3[CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[CH3:19]O>S(=O)(=O)(O)O>[CH3:19][O:15][C:14]([C:12]1[C:11]2[CH:17]=[C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:8]=[CH:9][C:10]=2[CH:13]=1)=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 21484415HCID 21484415, compound

Product 1

HCID 54520137HCID 54520137, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 15 g of 5-cyclohexyl-1-benzocyclobutenecarboxylic acid in 150 ml of absolute methanol and 1.5 ml of concentrated sulphuric acid is boiled for 14 hours under reflux whilst excluding water. The reaction mixture is evaporated in vacuo at 30° C to a volume of approx. 30 ml and the evaporation residue is partitioned between three times 200 ml of ether and twice 200 ml of ice water. The combined organic phases are successively washed with saturated sodium bicarbonate solution and water, dried over sodium sulphate and evaporated in vacuo. Distillation of the evaporation residue in a high vacuum yields 5-cyclohexyl-1-benzocyclobutenecarboxylic acid methyl ester in the fraction boiling at approx. 150° C/0.07 mm Hg.

Workup

  1. temperatureunder reflux
  2. customThe reaction mixture is evaporated in vacuo at 30° C to a volume of approx. 30 ml
  3. customthe evaporation residue is partitioned between three times 200 ml of ether and twice 200 ml of ice water
  4. washThe combined organic phases are successively washed with saturated sodium bicarbonate solution and water
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. distillationDistillation of the evaporation residue in a high vacuum

Sources & evidence

ORD record
ord-e0e306aef69a46398f4565672622381d
Source dataset
uspto-grants-1977_01
Patent number
US04004026

Reaction notes

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