Water → 2,3-Dihydro-3,3-dimethyl-2-(3-methylbutoxy)-5-benzofuranyl methanesulphonate

HRID 2071872Notes

Reaction equation

HRID 2071872 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([OH:14])[C:11]([CH3:16])([CH3:15])[C:10]=2[CH:17]=1)(=[O:4])=[O:3].[CH3:18][CH:19]([CH3:23])[CH2:20][CH2:21]O.O>S(=O)(=O)(O)O.C1C=CC=CC=1>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([O:14][CH2:21][CH2:20][CH:19]([CH3:23])[CH3:18])[C:11]([CH3:15])([CH3:16])[C:10]=2[CH:17]=1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 31260Isoamyl AlcoholHCID 536079(2-Hydroxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate

Product 1

HCID 214095582,3-Dihydro-3,3-dimethyl-2-(3-methylbutoxy)-5-benzofuranyl methanesulphonateYield 86%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran-5-yl methanesulphonate (13g, 0.05 mole), 3-methyl-1-butanol (4.4g, 0.05 mole) and concentrated sulphuric acid (4 drops) in benzene (50 ml) was heated at reflux under a Dean and Stark trap until 0.9 ml water (0.05 mole) had been eliminated. The reaction mixture was cooled, washed with dilute aqueous sodium hydroxide solution and with water (twice) and dried over sodium sulphate. The benzene was then distilled off under reduced pressure to give 2,3-dihydro-3,3-dimethyl-2-(3-methylbutoxy)-5-benzofuranyl methanesulphonate as a yellow oil (14 g, 86% yield) which slowly solidified (melting point 35°-38° C.).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. washwashed with dilute aqueous sodium hydroxide solution and with water (twice) and
  4. dry with materialdried over sodium sulphate
  5. distillationThe benzene was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-2a2c97a73a3c4fdeaacc03cf186c59c9
Source dataset
uspto-grants-1977_09
Patent number
US04049420

Reaction notes

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