2-Hydroxyisobutyric acid → 1-Carboxy-1-methylethyl [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetate

HRID 1732179Notes

Reaction equation

HRID 1732179 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14]2[CH:19]([CH2:20][CH3:21])[CH2:18][CH2:17][C:16](=[O:22])[CH:15]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].C(N1C=CN=C1)(N1C=CN=C1)=O.O[C:36]([CH3:41])([CH3:40])[C:37]([OH:39])=[O:38]>O1CCCC1>[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14]2[CH:19]([CH2:20][CH3:21])[CH2:18][CH2:17][C:16](=[O:22])[CH:15]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O:8][C:36]([C:37]([OH:39])=[O:38])([CH3:41])[CH3:40])=[O:7]

Participants

5

Reactant 3

HCID 116712-Hydroxyisobutyric acidHCID 682631,1'-CarbonyldiimidazoleHCID 10759778[2,3-Dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid

Product 1

HCID 137491121-Carboxy-1-methylethyl [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid (2.06 g, 0.006 mole) under nitrogen in tetrahydrofuran (THF) (50 ml) was added 1,1'-carbonyldiimidazole (0.97 g, 0.006 mole). The solution was stirred for 1 hour then 2-hydroxy-2-methylpropanoic acid (0.62 g, 0.006 mole) in THF (25 ml) was added and stirring was continued overnight. The THF was evaporated in vacuo and the residue chromatographed on silica (300 g) eluting with CH2Cl2 -THF-AcOH (100:2:1). Evaporation of the pertinent fractions gave 1-carboxy-1-methylethyl [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetate which melted at 167°-168° C.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe THF was evaporated in vacuo
  4. customthe residue chromatographed on silica (300 g)
  5. washeluting with CH2Cl2 -THF-AcOH (100:2:1)
  6. customEvaporation of the pertinent fractions

Sources & evidence

ORD record
ord-663265e3647247ce906107a758741647
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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