2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol

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

Procedure: In a similar fashion, nonobutyleneglycol (3-methyl-5-t-butyl-4-hydroxyphenyl)acetate can be prepared by substituting an equivalent amount of nonobutyleneglycol for octaethyleneglycol and substituting an equivalent amount of methyl (3-methyl-5-t-butyl-4-hydroxyphenyl)acetate for methyl 3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate in the above procedure.

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

Procedure: In a similar fashion, nonobutyleneglycol (3-methyl-5-t-butyl-4-hydroxyphenyl)acetate can be prepared by substituting an equivalent amount of nonobutyleneglycol for octaethyleneglycol and substituting an equivalent amount of methyl (3-methyl-5-t-butyl-4-hydroxyphenyl)acetate for methyl 3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate in the above procedure.

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

Procedure: 10% Pd/C (11.2 g) was added to MeOH (50 mL) at −15° C. in hydrogenation bottle under agron. BnO-dPEG8-OH (69.0 g, 0.15 mole) was added to the bottle along with MeOH (150 mL). The bottle was placed on the Parr shaker for 17 h at 50 psi of H2. The reaction was monitored by tlc on silica gel plates, eluting with 10% MeOH/CH2Cl2. The reaction is about 50% complete. The reaction was worked up. The reaction mixture was filter through glass fiber, used MeOH as needed to make a clean transfer. The filtrate was concentrated in vacuo to give an oil. A column was prepared with 600 g of silica gel and hexane. The crude product was placed onto column with hexane and minimum of TBME (100 mL). The column was eluted as follows: (2 L) 20% TBME/hexane; (2 L) 50% TBME/hexane; (4 L) TBME; (2 L) 5% MeOH/TBME; (2 L) 10% MeOH/TBME. Like fractions containing product were combined and concentrated in vacuo to give 28.5 g (51% yield). The product was characterized by nmr. eluting with 10% MeOH/CH2Cl2 The reaction mixture was filter through glass fiber The filtrate was concentrated in vacuo to give an oil The column was eluted Like fractions containing product concentrated in vacuo to give 28.5 g (51% yield)

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

Procedure: In a similar fashion, nonobutyleneglycol (3-methyl-5-t-butyl-4-hydroxyphenyl)acetate can be prepared by substituting an equivalent amount of nonobutyleneglycol for octaethyleneglycol and substituting an equivalent amount of methyl (3-methyl-5-t-butyl-4-hydroxyphenyl)acetate for methyl 3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate in the above procedure.