Catechol → 2,3-Dihydro-2,2-dimethyl-7-benzofuranol

HRID 2412815Notes

Reaction equation

HRID 2412815 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Cl[CH2:10][C:11]([CH3:13])=[CH2:12].[OH-].[Na+].COS([O:21][CH3:22])(=O)=O>O>[CH3:10][C:11]1([CH3:13])[CH2:12][C:8]2[CH:7]=[CH:6][CH:5]=[C:3]([OH:4])[C:1]=2[O:2]1.[CH3:12][C:11]1([CH3:13])[CH2:10][C:8]2[CH:7]=[CH:6][CH:5]=[C:3]([O:21][CH3:22])[C:1]=2[O:2]1

Participants

7

Reactant 4

HCID 289CatecholHCID 6497Dimethyl SulfateHCID 112413-Chloro-2-methyl-1-propeneHCID 14798Sodium Hydroxide

Product 2

HCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranolHCID 135313777-Methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material 2,3-dihydro-2,2-dimethyl-7-benzofuranol is prepared from catechol and 3-chloro-2-methylpropene as described by Neth. No. 6,500,340. The material (16.4 g) is added to 125 ml of water and contacted with 8 ml of 50% NaOH. After stirring one-half hour, 16.4 g of dimethylsulfate is added and the resulting suspension is stirred and heated at 60° for 2 hours. The resulting mixture is extracted with methylene chloride. The organic phase is dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residual oil is distilled to afford 2,3-dihydro-2,2-dimethyl-7-methoxybenzofuran.

Workup

  1. stirringthe resulting suspension is stirred
  2. temperatureheated at 60° for 2 hours
  3. extractionThe resulting mixture is extracted with methylene chloride
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. distillationThe residual oil is distilled

Sources & evidence

ORD record
ord-9046a6d532004c24910c15a895541ff3
Source dataset
uspto-grants-1985_01
Patent number
US04494979

Reaction notes

Loading…