Ethanol → HCID 20536243, compound

HRID 444079Notes

Reaction equation

HRID 444079 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([OH:10])[C:7]([CH3:12])([CH3:11])[C:6]=2[CH:13]=1.[CH2:14](O)[CH3:15]>S(=O)(=O)(O)O.C(N(CC)CC)C.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([O:10][CH2:14][CH3:15])[C:7]([CH3:11])([CH3:12])[C:6]=2[CH:13]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 205362245-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

Product 1

HCID 20536243HCID 20536243, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 8471TriethylamineCatalystHCID 3283Diethyl EtherSolvent

Procedure

5-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran (5 g, 0.02 mole) was heated under reflux in ethanol (30 ml) with sulphuric acid (4 drops) for 11/2 hour. The solution was cooled, neutralised with a few drops of triethylamine and run down. The residue was redissolved in ether and the solution washed with water, dried over magnesium sulphate and the solvent removed under vacuum leaving 4.7 g (86%) title product as a buff-coloured oil. The structure was confirmed by NMR.

Workup

  1. temperatureThe solution was cooled
  2. washthe solution washed with water
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-a8d35c412b0c473ab48114bf4aed092a
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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