δ-Damascone - Calculations

These calculations are to make 1Kg δ-Damascone from mesityl oxide

STEP 1 - Diels Alder

Suggested Cost
Raw Material MW Wt in g Wt in lbs
wt g (Aldrich)
Mesityl Oxide 98 123 1408.55
1,3-Pentadiene (56%) 68 540 6183.87
AlCl3 133 70 801.61
Toluene mL 600 6870.96
15% HCl mL 400 4580.64
Water mL 1000 11451.61

DA product 166 181 2072.74

109% by wt yield. * this is the amount of DA product that was useable after fractional distillation (min vac. 5 mm

STEP 2 - Epimerization
Suggested Cost
Raw Material MW Wt in g Wt in lbs
Wt g (Aldrich)
DA product 166 181 2072.74
KOH (pulverized) 56 10 114.52
Toluene (to transfer) mL 50 572.58
5% Brine solution mL 300 3435.48

Epimerized product 166 121 1385.64

* this is after fractional distillation. Vacuum 15 mmHg, 125C and 15:1 refulx ratio

STEP 3- Grignard
Suggested Cost
Raw Material MW Wt in g Wt in lbs
Wt g (Aldrich)
Mg 24 19.7 225.60
t-Butyl Methyl Ether mL 200 2290.32
isoPropyl MgBr mL 1.5 17.18
t-Butylchloride 92.5 72 824.52

STEP 4 - Aldol Condensation

Suggested Cost
Raw Material MW Wt in g Wt in lbs
Wt g (Aldrich)
 Epimer Ketone 166 108 1236.77
t-Butyl Methyl Ether mL 265 3034.68
Acetaldehyde 44 34.6 396.23
15% HCl mL 220 2519.35
Water mL 600 6870.96

STEP 4A- Dehydration

Suggested Cost
Raw Material MW Wt in g Wt in lbs
Wt g (Aldrich)
Aldol Product 209
5% Bicarbonate mL
Water mL
Product DD 192 87.324 1000
ulations
mascone from mesityl oxide

1.26

l distillation (min vac. 5 mm Hg)

5:1 refulx ratio

 moles

0.4548125
 δ-Damascone - Calculations
These calculations are to make 1Kg δ-Damascone from mesityl
Total
Raw Material Req Qty (g) Aldrich Cost solvents/water
mL
Mesityl Oxide 1409
1,3-Pentadiene (56%) 6184
AlCl3 802
Toluene (mL) 6875 7450
15% HCl (mL) 4585 7105
Water (mL) 11451 18322

DA product 2072
KOH (pulverized) 115
Toluene (to transfer) mL 575
5% Brine solution 3450

Epimerized product 1385

Mg 226
t-Butyl Methyl Ether (mL) 2300 5335
isoPropyl MgBr (mL) 17
t-Butylchloride 824

Epimer Ketone 1237

t-Butyl Methyl Ether (mL) 3035
Acetaldehyde 397
15% HCl (mL) 2520
Water (mL) 6871

At the end of this scale reaction(s) we get 1.0 Kg of distilled (98.5% purity by GC) δ-damascone. The end result is 7
yield.
lculations
amascone from mesityl oxide

scone. The end result is 79.18% wt/wt yield or 44% mole

wt yield or 44% mole