Diethyl Carbonate → HCID 53963170, compound

HRID 1578817Notes

Reaction equation

HRID 1578817 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[CH3:11][CH:12]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C:13](=[O:15])[CH3:14]>CCOCC>[CH3:11][CH:12]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C:13](=[O:15])[CH2:14][C:3]([O:7][CH2:8][CH3:9])=[O:10]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 54434397HCID 54434397, compound

Product 1

HCID 53963170HCID 53963170, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into ether (800 ml), 52% paraffin solution of sodium hydride (22.8 g) is suspended, and diethyl carbonate (89.4 g) is portionwise added thereto while cooling with ice in nitrogen stream. Then, 3,7,11-trimethyl-6,10-dodecadien-2-one (88 g) is dropwise added thereto. After refluxing for 15 hours, the reaction mixture is poured into ice water. The ether layer is separated, washed with water, dried and evaporated. The residue is distilled under reduced pressure to give ethyl 3,7,11-trimethyl-6,10-dodecadien-2-one-1-carboxylate (81 g). B.P. 130° to 135°C/0.05 mmHg. IR: 1640, 1675, 1710, 1740 cm-1. NMR (carbon tetrachloride): 1.10 (d), 1.29 (t), 1.60 (s), 1.68 (s), 1.98 (s), 2.00-2.80 (broad), 3.33 (s), 4.15 (q), 4.8-5.3 (broad).

Workup

  1. temperaturewhile cooling with ice in nitrogen stream
  2. temperatureAfter refluxing for 15 hours
  3. customThe ether layer is separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-43cb630fe28d4649bd5dc14ecaa96be7
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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