2,2-dimethyl-3H-1-benzofuran-7-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:70.01; pressure:0.00; stir:

Procedure: Dilution of the aliquot (2 uL) with DMSO (200 uL).

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:111.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preferably, in this step, the intermediate 2-(2-hydroxy-2-methylpropoxy)phenol is combined with para-toluensulfonic acid and toluene and heated to reflux (approximately 111° C.) to produce carbofuran phenol. heated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 200 ml. methylene-chloride 32.84 g. (0.2 mole) 2,3-dihydro-2,2-dimethyl-7-hydroxy-benzofuran, 57.37 g. (0.4 mole) 1-bromo-2-chloro-ethane 200 ml. 2N sodium hydroxide solution and 8 g. Adogen 464 phase transfer catalyst (tri-C8-10 -alkyl-methyl-ammonium-chloride) are added. The reaction mixture is heated under vigorous stirring for 7 hours and the reaction is monitored by gas chromatographic analysis. The reaction mixture is heated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 100 ml. ethylacetate 8.23 g. (0.05 mole) 2,3-dihydro-2,2-dimethyl-7-hydroxy-benzofuran, 14.3 g. (0.1 mole) 1-bromo-2-chloro-ethane, 6.9 g. (0.05 mole) anhydrous sodium carbonate and 8.3 (0.05 mole) potassium iodide are added. The reaction mixture is heated for 30 hours and the reaction is monitored by gas chromatographic analysis. The reaction mixture is heated for 30 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 100 ml. ethylacetate 8.23 g. (0.05 mole) 2,3-dihydro-2,2-dimethyl-7-hydroxy-benzofuran, 14.3 g. (0.1 mole) 1-bromo-2-chloro-ethane, 6.9 g. (0.05 mole) anhydrous sodium carbonate and 8.3 (0.05 mole) potassium iodide are added. The reaction mixture is heated for 30 hours and the reaction is monitored by gas chromatographic analysis. The reaction mixture is heated for 30 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution containing 32.83 g of 1,2,3-trichloro-5-nitrobenzene and 26.11 g of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran in 300 ml of methyl ethyl ketone under an atmosphere of nitrogen and at room temperature was added 21.98 g of anhydrous potassium carbonate. The reaction mixture was heated to reflux. Reflux was maintained for 30 hrs. The reaction mixture was cooled to room temperature and the solvents removed. The tan solid residue was dissolved in hot hexane containing a little ethyl acetate. This was filtered and the filtrate allowed to cool to room temperature then placed in freezer to cool further to promote crystallization. The crystals were collected and placed in a vacuum dessicator for drying. A second crop of crystals was obtained from the mother liquors. This afforded 29.2 g of pale tan crystals. mp 105°-110° C. NMR (CDCl3): 1.47 (s, 6H), 3.03 (s, 2H), 6.3-7.0 (m, 3H), 8.22 (s, 2H). The reaction mixture was heated to reflux Reflux was maintained for 30 hrs the solvents removed The tan solid residue was dissolved in hot hexane containing a little ethyl acetate This was filtered to cool to room temperature to cool further crystallization The crystals were collected for drying A second crop of crystals was obtained from the mother liquors