2,2,4-trimethylpentane-1,3-diol

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

Procedure: Into a 3-liter four neck flask equipped with stirrer, thermometer, a nitrogen inlet tube, Dean-Stark trap and condenser was charged 492 grams (3.36 moles) of 2,2,4-trimethyl-1,3-pentanediol; 963 grams n-heptanoic acid (7.40 moles) and 0.1 wt. percent of dibutyl tin oxide as catalyst. The reaction was carried out under reflux conditions at 220° C. to a hydroxyl value <2.0. The excess heptanoic acid was stripped under reduced pressure for a TAN <1.0. The ester was subsequently treated with concentrated caustic, stripped and filtered to yield 1170 grams of 2,2,4-trimethyl-1,3-pentanediol di-n-heptanoate. with concentrated caustic filtered

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

Procedure: Treatment of 2,2,4-trimethylpentan-1,3-diol with prenyl chloride employing the alkylation reaction conditions described above provided 1-(3-methyl-2-butenyloxy)-2,2,4-trimethylpentan-3-ol in 92.0% yield (393.8 g, b.p.=82–84 C./0.8 mmHg).

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

Procedure: Treatment of 2,2,4-trimethylpentan-1,3-diol with prenyl chloride employing the alkylation reaction conditions described above provided 1-(3-methyl-2-butenyloxy)-2,2,4-trimethylpentan-3-ol in 92.0% yield (393.8 g, b.p.=82–84 C./0.8 mmHg).

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

Procedure: Treatment of 2,2,4-trimethylpentan-1,3-diol with isobutyl bromide employing the alkylation reaction conditions described above provided 1-(2-methylpropyloxy)-2,2,4-trimethylpentan-3-ol in 88.0% yield (355.5 g, b.p.=81–82 C./2.5 mmHg).

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

Procedure: Treatment of 2,2,4-trimethylpentan-1,3-diol with ethyl bromide employing the alkylation reaction conditions described above provided 1-ethoxy-2,2,4-trimethylpentan-3-ol in 90.0% yield (313.2 g, b.p.=79–80 C./3.2 mmHg).

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

Procedure: Treatment of 2,2,4-trimethylpentan-1,3-diol with ethyl bromide employing the alkylation reaction conditions described above provided 1-ethoxy-2,2,4-trimethylpentan-3-ol in 90.0% yield (313.2 g, b.p.=79–80 C./3.2 mmHg).

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1 L flask equipped with a reflux condenser and a thermometer, was added 292.5 g (2.0 mol) of 2,2,4-trimethylpentan-1,3-diol, 352.0 g (4.4 mol) of 50% aqueous NaOH, and 6.45 g (20 mmol) of tetrabutyl ammonium bromide. This mixture was heated in an oil bath and when the reaction mixture reached 50° C., 199.2 g (2.2 mol) of methallyl chloride was added drop-wise over 50 minutes. During the addition, the oil bath temperature was gradually raised to 100° C. and the reaction was continued for an additional 3 hours at 100° C. The reaction mixture was cooled, quenched with 400 ml of water, and extracted twice with 100 ml of toluene. The combined organic layers were washed with 50 ml of saturated ammonium chloride and 50 ml of saturated sodium chloride and evaporated to give 408 g of crude 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol. After reduced pressure distillation (71–80° C., 3 mmHg), 377.1 g (yield 94.1%) of 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol was obtained. To a 1 L flask equipped with a reflux condenser This mixture was heated in an oil bath reached 50° C. During the addition The reaction mixture was cooled quenched with 400 ml of water extracted twice with 100 ml of toluene The combined organic layers were washed with 50 ml of saturated ammonium chloride and 50 ml of saturated sodium chloride evaporated

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

Procedure: Prepared as in Example 215c from 2,2,4-trimethylpentane-1,3-diol and 2,6-dinitrobenzonitrile in 90% yield. MS 293 (MH+).

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

Procedure: Prepared as in Example 215c from 2,2,4-trimethylpentane-1,3-diol and 2,6-dinitrobenzonitrile in 90% yield. MS 293 (MH+).

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

Procedure: 146 g (1 mol) 2,2,4-trimethyl-1,3-dihydroxypentane, 346.5 g (2.2 mols) 4-nitrochlorobenzene and 140 g powdered sodium hydroxide were reacted using the same procedure described in Example 1 in 600 ml DMSO. were reacted

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

Procedure: 146 g (1 mol) 2,2,4-trimethyl-1,3-dihydroxypentane, 346.5 g (2.2 mols) 4-nitrochlorobenzene and 140 g powdered sodium hydroxide were reacted using the same procedure described in Example 1 in 600 ml DMSO. were reacted

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1-liter round bottom flask was charged 2,2,4,4-tetramethyl-1,3-cyclobutanedione (140.2 g, 1.0 moles), TMPD glycol (146.2 g, 1.0 moles) and potassium carbonate (73 g, 0.53 moles). The mixture was heated to 120° C. and held for 4 hours. Reaction was cooled and 200 mL of toluene added. Organic layer was washed 4 times at 70° C. Toluene removed to provide 275 g of product. GC assay of the product was 95.9% (4.6:1 mixture of two major isomers). Reaction was cooled Organic layer was washed 4 times at 70° C Toluene removed