2,4-Dichlorophenol → ethyl (R)-2-(2,4-dichlorophenoxy)propionate

HRID 1400242Notes

Reaction equation

HRID 1400242 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10]([O:15][CH2:16][CH3:17])(=[O:14])[C@H:11]([CH3:13])O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C@H:11]([CH3:13])[C:10]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 84492,4-Dichlorophenol2×HCID 11776TriphenylphosphineHCID 92831(L)-ethyl lactate2×HCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 12375251ethyl (R)-2-(2,4-dichlorophenoxy)propionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichlorophenol (compound 3; 3.0 g, 18.4 mmol), ethyl (S)-lactate (compound 8a; 2.39 g, 20.2 mmol, 1.1 eq), and triphenylphosphine (7.23 g, 27.6 mmol, 1.5 eq) in anhydrous THF (50 mL), diisopropylazodicarboxylate (5.46 g, 27.6 mmol, 1.5 eq) was added dropwise. The reaction mixture was stirred 16 hours at room temperature. The solvent was evaporated and the resulting residue was subjected to chromatography on silica gel with 2-5% EtOAc/hexanes. Product-containing fractions were pooled and evaporated to yield a pale yellow oil which was used without further purification: 1H NMR (CDCl3) δ 7.31 (d, 1H), 7.06 (dd, 1H), 6.75 (d, 1H), 4.70 (q, 1H), 4.21 (dq, 2H), 1.62 (d, 3H), 1.20 (t, 3H).

Workup

  1. customThe solvent was evaporated
  2. customevaporated
  3. customto yield a pale yellow oil which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-373f11f920ba46839f66fae6e44a4dc8
Source dataset
uspto-grants-2014_12
Patent number
US08906945B2

Reaction notes

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