(2E,4E)-hexa-2,4-dienoyl chloride

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

Procedure: 50 g (120 mmol; 1 eq.) of 6-O-palmitoyl-L-ascorbic acid were dissolved in 400 ml of pyridine in a 1 l 4-necked flask. 23.40 g (130 mmol; 1.1 eq.) of sorboyl chloride, dissolved in 30 ml of dichloromethane, were slowly added dropwise at an internal temperature of -15° C. Care was taken here that the internal temperature did not exceed -10° C. The mixture was brought to room temperature and additionally stirred for 2 hours. The reaction solution was concentrated on a rotary evaporator and then codistilled with toluene. The residue was taken up in a little dichloromethane and extracted with 1 M HCl. The organic phase was concentrated somewhat and treated with an excess of n-hexane. A white precipitate was deposited, which was dried in an oil pump vacuum. were slowly added dropwise at an internal temperature of -15° C did not exceed -10° C was brought to room temperature The reaction solution was concentrated on a rotary evaporator extracted with 1 M HCl The organic phase was concentrated somewhat treated with an excess of n-hexane which was dried in an oil pump vacuum

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

Procedure: Sorboyl chloride (3.53 g) was added to a mixture of 4.0 g of N-allylphenethylamine, 25 mL of methylene chloride and 25 mL of 15% aqueous sodium hydroxide, keeping the temperature below 15°. The mixture was stirred in an ice bath for 1 hour, then at room temperature overnight. The aqueous layer was extracted several times with toluene and the combined organic phases were washed successively with 5% hydrochloric acid, water, and 10% sodium carbonate solution. Removal of the solvents gave 6.37 g of N-allyl-N-phenethylsorbamide. This product was heated under reflux in 50 mL of p-xylene for 10 hours. Removal of the solvent gave 6-methyl-3a,4,5,7a-tetrahydroisoindolin-1-one as a mixture of isomers still containing about 10% of the uncyclized starting material. the temperature below 15° at room temperature overnight The aqueous layer was extracted several times with toluene the combined organic phases were washed successively with 5% hydrochloric acid, water, and 10% sodium carbonate solution Removal of the solvents

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

Procedure: A solution of 0.9 g (6.9 mmol) of sorboyl chloride in 6 mL of THF was added slowly with stirring to a mixture of 1.87 g (6.9 mmol) of n-octadecanol in 10 mL of THF at 40° C. The resulting mixture was refluxed for 16 hours. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel using chloroform as eluent. The appropriate fractions were combined and evaporated to dryness in vacuo to give a white solid product: 1.04 g (42%) yield. TLC (CHCl3)Rf=0.75. 1H NMR (300 MHz) δ 0.89 [3H, t, —(CH3)15CH3)],1.25 [30H, br m, —(CH3)15—], 1.62 [2H, t, —OCH2CH2—], 1.86 [3H, d, CH3CH═], 4.14 [2H, t, —OCH2—], 5.79 [1H, d, OCCH═], 6.19 [2H, m, CH3CH═CH—], 7.22 [1H, m, CH3CH═CH—CH═]. The resulting mixture was refluxed for 16 hours The solvent was evaporated under reduced pressure the crude product was purified by column chromatography on silica gel evaporated to dryness in vacuo to give a white solid product 1.04 g (42%) yield

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

Procedure: Sorboyl chloride (3.53 g) was added to a mixture of 4.0 g of N-allylphenethylamine, 25 mL of methylene chloride and 25 mL of 15% aqueous sodium hydroxide, keeping the temperatue below 15°. The mixture was stirred in an ice bath for 1 hour, then at room temperature overnight. The aqueous layer was extracted several times with toluene and the combined organic phases were washed successively with 5% hydrochloric acid, water, and 10% sodium carbonate solution. Removal of the solvents gave 6.37 g of N-allyl-N-phenethylsorbamide. This product was heated under reflux in 50 mL of p-xylene for 10 hours. Removal of the solvent gave 6-methyl-3a,4,5,7a-tetrahydroisoindolin-1-one as a mixture of isomers still containing about 10% of the uncyclized starting material. the temperatue below 15° at room temperature overnight The aqueous layer was extracted several times with toluene the combined organic phases were washed successively with 5% hydrochloric acid, water, and 10% sodium carbonate solution Removal of the solvents