4-Chloro-3-methylphenol → Methyl (2R)-2-(4-chloro-3-methylphenoxy)propanoate

HRID 456810Notes

Reaction equation

HRID 456810 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:29]([O:34][CH3:35])(=[O:33])[C@H:30]([CH3:32])O.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][C@H:30]([CH3:32])[C:29]([O:34][CH3:35])=[O:33])=[CH:3][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 17324-Chloro-3-methylphenolHCID 11776TriphenylphosphineHCID 94386methyl (S)-lactateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 58818328Methyl (2R)-2-(4-chloro-3-methylphenoxy)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-4-chlorophenol (10.0 g, 69 mmol), triphenylphosphine (1.3 eq, 22 g), (S)-methyl lactate (1.3 eq, 9.4 mL) in DCM (230 mL) at 0° C. was added DEAD (1.2 eq, 13 mL) over 1 min. Reaction warmed to rt overnight. The mixture was then filtered through a pad of silica gel and concentrated. The residue was purified via flash chromatography eluting with 10% EtOAc/hexanes to provide the product as a colorless oil.

Workup

  1. customReaction
  2. filtrationThe mixture was then filtered through a pad of silica gel
  3. concentrationconcentrated
  4. customThe residue was purified via flash chromatography
  5. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-9f55e57fcfe743d9a70829e7a0be8d4c
Source dataset
uspto-grants-2007_03
Patent number
US07186746B2

Reaction notes

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