Methanol → 3-Methoxycarbonylmethylchroman

HRID 1032391Notes

Reaction equation

HRID 1032391 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-54de060bfc0e484fa9e43be7d89c5713
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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