Methanol → 3-Methoxycarbonylmethylchroman

HRID 1196010Notes

Reaction equation

HRID 1196010 reaction equation
S(=O)(=O)(O)O.[C:6]([CH2:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12][CH2:11]1)([OH:8])=[O:7].[CH3:20]O>>[CH3:20][O:7][C:6]([CH2:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12][CH2:11]1)=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 148384122-(3,4-dihydro-2H-1-benzopyran-3-yl)acetic acid

Product 1

HCID 148384133-MethoxycarbonylmethylchromanYield 98%

Procedure

1.5 ml of sulphuric acid (100% strength) are added to a solution of 7.69 g (40 mmol) of 3-carboxymethylchroman in 150 ml of methanol and the whole is boiled under reflux for 3 hours. After cooling, the reaction mixture is concentrated by evaporation in vacuo. The residue is dissolved in diethyl ether and washed, while cold, with water, sodium hydrogen carbonate and again with water. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. 8.08 g (98%) of 3-methoxycarbonylmethylchroman are obtained in the form of a pale yellow oil.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated by evaporation in vacuo
  4. dissolutionThe residue is dissolved in diethyl ether
  5. washwashed
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-52962c21f3784c67b8f602b2a3cc036f
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

Loading…