1-methyl-4-propan-2-ylidenecyclohexene

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

Procedure: The hydroperoxide resulting from terpinolene can be reduced to p-mentha-1,8-dien-4-ol and this can be selectively catalytically hydrogenated to give 4-terpineol.

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

Procedure: 9,10-Bis(3-methylanilino)phenanthrene was mixed in an amount of 6.6 g (17.0 mmol) with 14.8 g (68.0 mmol) of m-iodotoluene, 3.82 g (68 mmol) of potassium hydroxide, 0.98 g (6.8 mmol) of copper-(I) bromide, 2.52 g (6.8 mmol) of ethyltriphenylphosphonium bromide, and 10 mL of terpinolene. This mixture was reacted at 115-125° C. for 2 hours in a nitrogen stream. After the reaction, the reaction solvent was distilled off by vacuum concentration. To the residue were added 5 mL of toluene, 67 mL of ethyl acetate, and 22 mL of water. The resultant mixture was subjected to liquid separation. To the organic layer was added 71 mL of methanol. The resultant solution was cooled for crystallization. Thus, the target compound (I-22) was obtained as light-yellow crude crystals in an amount of 9.0 g (yield, 93.0%). The target compound obtained had a melting point of 223-224° C. and a content as determined by HPLC of 99.6% (HPLC conditions: column, YMC-A-312; eluent, methanol/tetrahydrofuran (V/V=99/1); detection UV, 254 nm; flow rate, 1.0 mL/min). This mixture was reacted at 115-125° C. for 2 hours in a nitrogen stream After the reaction the reaction solvent was distilled off by vacuum concentration To the residue were added 5 mL of toluene, 67 mL of ethyl acetate, and 22 mL of water The resultant mixture was subjected to liquid separation To the organic layer was added 71 mL of methanol The resultant solution was cooled for crystallization Thus, the target compound (I-22) was obtained as light-yellow crude crystals in an amount of 9.0 g (yield, 93.0%) The target compound obtained

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

Procedure: The hydroperoxide resulting from terpinolene can be reduced to p-mentha-1,8-dien-4-ol and this can be selectively catalytically hydrogenated to give 4-terpineol.

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

Procedure: The hydroperoxide resulting from terpinolene can be reduced to p-mentha-1,8-dien-4-ol and this can be selectively catalytically hydrogenated to give 4-terpineol.

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

Procedure: Crude pine oil (138.8 g; dehydrated by vacuum stripping and containing terpineol: 94.0%; fenchol: 0.29%; borneol: 3.66%) is heated with ME-810 (12.4 g; mixture of methyl fatty acid esters, available from Peter Cremer NA, LP) and methanesulfonic acid (1.0 g) at 100° C., 30-60 mm Hg for 10 h. GC of the reaction mixture shows: terpineol: 19.9%; borneol: 1.85%; terpene alcohol fatty esters: 2%. Limonene and terpinolene, formed by acid-catalyzed dehydration of terpineol, account for 65% of the reaction mixture. Distillation of the reaction mixture gives 108 g of material containing 1.85% of borneol and 18.5% of terpineol. This example shows that methanesulfonic acid is an unacceptable catalyst for the transesterification.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Blend C Copolymer--Into a polymerization reactor equipped with an agitator and a reflux condenser were charged 770 ml of styrene, 4 grams of terpinolene, 200 ml of ethylbenzene and 200 ml of methyl ethyl ketone. Then 100 grams of medium cis-polybutadiene from Firestone Tire & Rubber Company (Diene 35) was dissolved in the mixture. After the rubber had dissolved, 50 ml of acrylic acid was added to the mixture. The temperature of the reaction mixture was raised to 80° C. and maintained between 80° and 120° C. during the course of the polymerization. Polymerization was initiated by introducing into the system a mixture of 0.3 ml of tert-butyl peracetate and 0.3 ml of tert-butyl per-neo-decanoate. About 1.5 hours later, continuous addition of 50 ml of acrylic acid was initiated and this addition was continued for about 5 hours. Additional 0.3 ml portions of tert-butyl peracetate were introduced into the polymerization mixture at 135 minutes and 270 minutes after the initiation of polymerization. To control the viscosity of the reaction mixture, 350 ml of methyl ethyl ketone was added from 315 minutes to 390 minutes after initiation of polymerization. Polymerization was terminated about 6.75 hours after initiation and a solution of two grams of 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-benzene and 0.5 gram of tris(nonylphenyl)phosphite dissolved in 100 ml of methyl ethyl ketone was added. The resultant polymer was recovered and dried, first in air and then in a vacuum oven, to yield 660 grams of rubber-modified styrene-acrylic acid graft copolymer. The resultant polymer contained about 85.6% styrene and about 14.4% acrylic acid. Its rubber content was approximately 15.1% based on the weight of the resin phase. Blend C Copolymer--Into a polymerization reactor equipped with an agitator and a reflux condenser After the rubber had dissolved maintained between 80° and 120° C. during the course of the polymerization Polymerization by introducing into the system this addition was continued for about 5 hours after the initiation of polymerization was added from 315 minutes to 390 minutes after initiation of polymerization Polymerization was terminated about 6.75 hours after initiation a solution of two grams of 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-benzene and 0.5 gram of tris(nonylphenyl)phosphite dissolved in 100 ml of methyl ethyl ketone was added The resultant polymer was recovered dried, first in air

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

Procedure: 9,10-Bis(3-methylanilino)phenanthrene was mixed in an amount of 6.6 g (17.0 mmol) with 14.8 g (68.0 mmol) of m-iodotoluene, 3.82 g (68 mmol) of potassium hydroxide, 0.98 g (6.8 mmol) of copper-(I) bromide, 2.52 g (6.8 mmol) of ethyltriphenylphosphonium bromide, and 10 mL of terpinolene. This mixture was reacted at 115-125° C. for 2 hours in a nitrogen stream. After the reaction, the reaction solvent was distilled off by vacuum concentration. To the residue were added 5 mL of toluene, 67 mL of ethyl acetate, and 22 mL of water. The resultant mixture was subjected to liquid separation. To the organic layer was added 71 mL of methanol. The resultant solution was cooled for crystallization. Thus, the target compound (I-22) was obtained as light-yellow crude crystals in an amount of 9.0 g (yield, 93.0%). The target compound obtained had a melting point of 223-224° C. and a content as determined by HPLC of 99.6% (HPLC conditions: column, YMC-A-312; eluent, methanol/tetrahydrofuran (V/V=99/1); detection UV, 254 nm; flow rate, 1.0 mL/min). This mixture was reacted at 115-125° C. for 2 hours in a nitrogen stream After the reaction the reaction solvent was distilled off by vacuum concentration To the residue were added 5 mL of toluene, 67 mL of ethyl acetate, and 22 mL of water The resultant mixture was subjected to liquid separation To the organic layer was added 71 mL of methanol The resultant solution was cooled for crystallization Thus, the target compound (I-22) was obtained as light-yellow crude crystals in an amount of 9.0 g (yield, 93.0%) The target compound obtained