Sodium Carbonate → 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal

HRID 1259006Notes

Reaction equation

HRID 1259006 reaction equation
[CH2:1]([O:19][CH:20]([CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:21][OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:1]([O:19][CH:20]([CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:21]=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 58264329HCID 58264329, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 866675312,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanalYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol (4.0 g, 7.0 mmol) and PCC (4.5 g, 21.0 mmol) in dichloromethane (75 mL) was added sodium carbonate (375 mg, 3.5 mmol). The solution was stirred for 6 hours at room temperature then filtered through silica with diethyl ether rinses (250 mL). The filtrate was concentrated in vacuo to dryness and purified by column chromatography on silica gel 60 (eluted with a gradient of 100% hexanes to 5% ether in hexanes) to afford 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal as a colorless oil (1.6 g, 39%)

Workup

  1. filtrationthen filtered through silica with diethyl ether rinses (250 mL)
  2. concentrationThe filtrate was concentrated in vacuo to dryness
  3. custompurified by column chromatography on silica gel 60 (
  4. washeluted with a gradient of 100% hexanes to 5% ether in hexanes)

Sources & evidence

ORD record
ord-947886f728cf4cb39c665b350d7484b6
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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