n-Dodecylammonium thiocyanate

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:0.00; pressure:0.00; stir:

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:; See reaction.notes.procedure_details.

Procedure: A solution of 50 g (0.32 mole) of 2,5-dihydroxybenzoic acid in 260 ml of methanol, at 0° C., was combined with 33 ml of sulphuric acid. The resulting solution was heated to 70° C. under stirring. After 6 hours the reaction mixture was cooled to room temperature and concentrated to small volume under vacuum. The resulting oily layer was taken up with sodium hydroxyde 5N and extracted with ethyl acetate the organic layer was washed with water, dried over sodium sulphate and evaporated under vacuum, to provide 52 g of methyl 2,5-dihydroxybenzoate which were used in the next step as obtained. at 0° C. After 6 hours the reaction mixture was cooled to room temperature concentrated to small volume under vacuum extracted with ethyl acetate the organic layer was washed with water dried over sodium sulphate evaporated under vacuum

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

Procedure: Synthesis was carried out in the same manner as in Example 1, except for replacing methyl 2,4-dihydroxybenzoate with methyl 2,5-dihydroxybenzoate and replacing 2-ethylhexyl bromide with n-hexyl bromide, to obtain methyl 5-n-hexyloxy-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 12) as a colorless, clear and oily substance in a yield of 58%. The analytical results are shown below. ##STR33## Synthesis

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

Procedure: Synthesis was carried out in the same manner as in Example 1, except for replacing methyl 2,4-dihydroxybenzoate with methyl 2,5-dihydroxybenzoate and replacing 2-ethylhexyl bromide with n-hexyl bromide, to obtain methyl 5-n-hexyloxy-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 12) as a colorless, clear and oily substance in a yield of 58%. The analytical results are shown below. ##STR33## Synthesis

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

Procedure: Synthesis was carried out in the same manner as in Example 1, except for replacing methyl 2,4-dihydroxybenzoate with methyl 2,5-dihydroxybenzoate and replacing 2-ethylhexyl bromide with 2-cyclohexylethyl p-toluenesulfonate, to obtain methyl 5-(2-cyclohexylethoxy)-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 11) as a pale yellow solid in a yield of 43%. The analytical results are shown below. ##STR32## Synthesis

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

Procedure: Synthesis was carried out in the same manner as in Example 1, except for replacing methyl 2,4-dihydroxybenzoate with methyl 2,5-dihydroxybenzoate and replacing 2-ethylhexyl bromide with 2-cyclohexylethyl p-toluenesulfonate, to obtain methyl 5-(2-cyclohexylethoxy)-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 11) as a pale yellow solid in a yield of 43%. The analytical results are shown below. ##STR32## Synthesis