Toluene → HCID 18509354, compound

HRID 1356580Notes

Reaction equation

HRID 1356580 reaction equation
C([O:4][C:5]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([O:13]C)=[O:12])[C:6]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=O)C.C1(C)C=CC=CC=1.C(OO)(=O)C>O>[CH2:15]([C:6]12[C:5](=[O:4])[CH2:9][CH2:8][CH:7]1[CH2:10][C:11](=[O:13])[O:12]2)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6585Peracetic Acid2×HCID 1173725357374-49-9

Product 1

HCID 18509354HCID 18509354, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2000 ml three-necked round-bottom flask, equipped with a magnetic stirrer, nitrogen device, thermometer, dropping funnel and a reflux condenser was charged with 591.0 g of crude methyl 3-acetoxy-2-pentyl-2-cyclopentene-1-acetate and 70 g of toluene. At 26° C. 386.9 g (2.04 mol) 40% peracetic acid were added dropwise over a 5.3 h period. Stirring was continued for 2 h. 22.0 g (0.12 mol) of 40% peracetic acid were added over 30 min, and stirring was continued for another 2 h. 350 g of water were added and the water-layer (590.4 g) was separated. Three more washes were made with each 350 ml of water. The organic phase (1273.9 g) was evaporated to give 437.8 g of crude product which was vacuum distilled (0.4 hPa) to furnish 2 fractions, of which the first one (Bp=90-144° C.) was 172.55 g, containing 26.5% of product and the second one was 187.6 g, containing 95% of lactone. 1H-NMR: 0.88 (br t, J=6.7 Hz, Me); 1.15-1.45 (m, 6H); 1.67-1.87 (m, 3H); 2.14-2.63 of overlapping m, 4H); 2.84-2.97 (m, 2H). 13C-NMR: 13.9 (Me), 22.4, 22.6, 25.0, 31.9, 33.0, 35.7, 35.8 (CH2), 38.6 (CH), 89.0 (C), 175.0 (CO2), 210.9 (CO). MS: M+=210 (5): 154 (16), 139 (22), 112 (25), 111 (73), 99 (79), 98 (100), 83 (26), 71 (26), 55 (73), 43 (28).

Workup

  1. customA 2000 ml three-necked round-bottom flask, equipped with a magnetic stirrer
  2. customAt 26° C
  3. stirringstirring
  4. waitwas continued for another 2 h
  5. customthe water-layer (590.4 g) was separated
  6. customThe organic phase (1273.9 g) was evaporated

Sources & evidence

ORD record
ord-d7ce74e0d88d45fbbbbdad487a24c3fe
Source dataset
uspto-grants-2003_07
Patent number
US06586620B1

Reaction notes

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