Water → HCID 53891839, compound

HRID 1646148Notes

Reaction equation

HRID 1646148 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C.[CH:22]1([OH:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=[CH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.O>C(OCC)C>[C:1]([O:38][CH:22]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=[CH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 53721826HCID 53721826, compound

Product 1

HCID 53891839HCID 53891839, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.8 g of dodecanoyl chloride and 2.0 ml of triethylamine are added to a solution of 1.65 g of 8-cyclohexadecen-1-ol in 25 ml of diethyl ether. After heating to reflux for 5 hours, the mixture is poured into 100 ml of H2O, the organic phase is separated off, the aqueous phase is extracted with 25 ml of diethyl ether, and the combined organic phases are evaporated in vacuo. Purification of the residue by chromatography on silica gel using dichloromethane/hexane 1:3 gives 1.05 g of 8-cyclohexadecen-1-yl dodecanoate as a viscous oil.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 5 hours
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted with 25 ml of diethyl ether
  5. customthe combined organic phases are evaporated in vacuo
  6. customPurification of the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-87d56f09513d4476a5a4154e30c531d5
Source dataset
uspto-grants-1993_01
Patent number
US05178792

Reaction notes

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