Acetic Acid → Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionate

HRID 857205Notes

Reaction equation

HRID 857205 reaction equation
[O:1]1[CH2:18][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13].[Cl-:19].[Li+].C(O)(=O)C>O1CCCC1>[Cl:19][CH2:18][CH:2]([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 21866634Methyl 2-(8,9-epoxynonyloxy)-2-methylpropionate

Product 1

HCID 21866631Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionateYield 106.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(8,9-epoxynonyloxy)-2-methylpropionate (26 g) was dissolved in 260 ml of dry tetrahydrofuran, and 6.8 g of lithium chloride and 7 g of acetic acid were added and the mixture was stirred for 22 hours at room temperature. The reaction solution was poured into ice-cold water, extracted with ethyl acetate, washed with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated to give 31.7 g of the objective compound as oil.

Workup

  1. additionThe reaction solution was poured into ice-cold water
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3192df9d44124557871825d8bef55cf5
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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