[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([C:8]([CH3:11])([CH3:10])[OH:9])[CH:7]=1.[NH2-].[Na+].Cl[CH:16](Cl)[C:17]([O-:19])=[O:18].[K+].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:12][CH:16]([C:17]([OH:19])=[O:18])[O:9][C:8]([CH3:10])([CH3:11])[C:6]=2[CH:7]=1A solution of 1.9 g of 5-chloro-α,α-dimethyl-2-hydroxybenzene-methanol in 15 ml of toluene was added dropwise to a stirred mixture of 0.8 g of sodium amide and 100 ml of toluene and the mixture was refluxed for 5 hours and was cooled to 50° C. 2 g of potassium dichloroacetate were added thereto and the mixture was refluxed for 6 hours and was cooled to 20° C. The mixture was poured into 200 ml of ice and 100 ml of N hydrochloric acid. The decanted aqueous phase was extracted 3 times with 50 ml of ether and the combined organic phases were made alkaline by stirring with 100 ml of 2 N sodium hydroxide solution. The organic phase was washed 3 times with 50 ml of N sodium hydroxide solution and the aqueous phase was acidified with concentrated hydrochloric acid and was extracted 3 times with 100 ml of ether. The ether phase was treated with 100 ml of 10% aqueous sodium bicarbonate solution and the aqueous phase was acidified with concentrated hydrochloric acid and was extracted 3 times with 50 ml of methylene chloride. The organic phase was washed with water until neutral, dried over magnesium sulfate and evaporated to dryness to obtain 2.1 g of 6-chloro-4,4-dimethyl-[4H]-1,3-benzodioxin-2-carboxylic acid which after crystallization from cyclohexane melted at 142° C.
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