Benzene, (3,3-diethoxy-1-propenyl)- → HCID 54092539, compound

HRID 1491565Notes

Reaction equation

HRID 1491565 reaction equation
C(O[CH:4](OCC)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[C:16]([C@@H:21]([C@H:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[OH:24])[OH:22])([O:18][CH2:19][CH3:20])=[O:17]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1(C)C=CC=CC=1>[C:7]1([CH:6]=[CH:5][CH:4]2[O:24][C@@H:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C@H:21]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:22]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 91340Benzene, (3,3-diethoxy-1-propenyl)-HCID 6993580Diethyl tartrate

Product 1

HCID 54092539HCID 54092539, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of cinnamaldehyde diethylacetal (223.0 g, 1.08 mol), diethyl L-tartrate (290 g, 1.41 mol), toluene (1100 g) and pyridinium p-toluenesulfonate (1.7 g) was heated at 92°-110° C. for a 6 hour period. During the heating period, volatiles (250-300 mL) were removed by distillation through an 8" Vigreaux column. The mixture was cooled (25° C.) and washed with aqueous sodium bicarbonate solution (350 mL) and brine (4×200 mL). Evaporation of solvents and crystallization of the residue gave 250 g (72.3% yield) of (4R,5R)-2-(2-phenyl-1-ethenyl)-4,5-dicarboethoxy-1-3-dioxolane, mp 55.5°-56° C., [α]D25 -5.2° (c,0.1,methanol) 1H-NMR (CDCl3)δ7.45-7.26 (5H,m), 6.86 (1H,d, J=16.1 Hz), 6.26 (1H,dd,J=6.8 Hz and 16.1 Hz), 5.82 (1H,d,J=6.8 Hz), 4.87 (1H,d,J=3.6 Hz), 4.78 (1H,d,J=3.6 Hz), 4.36-4.26 (4H,2 q, overlapping J=7.1 Hz), 1.38-1.31 (6H, 2 t, overlapping, J=7.1 Hz). IR(KBr) 2970,2890,1745,1720,1450,1410 cm.-1MS m/e (% abundance) 320(2), 247(6), 148 (38), 131(78), 115(100), 95(80), 91(8), 77(15), 55(14).

Workup

  1. temperaturewas heated at 92°-110° C. for a 6 hour period
  2. customDuring the heating period, volatiles (250-300 mL) were removed by distillation through an 8" Vigreaux column
  3. washwashed with aqueous sodium bicarbonate solution (350 mL) and brine (4×200 mL)
  4. customEvaporation of solvents and crystallization of the residue

Sources & evidence

ORD record
ord-6b6240034c95493b9724213c1978b1dd
Source dataset
uspto-grants-1994_12
Patent number
US05371069

Reaction notes

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