HCID 59627701, compound → HCID 59627640, compound

HRID 1930117Notes

Reaction equation

HRID 1930117 reaction equation
[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]([CH3:15])=[C:6]([C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1>CC(O)=O.[Zn]>[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]([CH3:15])=[C:6]([CH:8]([OH:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1

Participants

4

Reactant 1

HCID 59627701HCID 59627701, compound2×

Product 1

HCID 59627640HCID 59627640, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)-2-oxoacetate (Intermediate 3-7; 6.12 g, 23.84 mmol) in warm AcOH (60 mL) was added to a stirred suspension of zinc dust (7.80 g, 119.21 mmol) in AcOH (20 mL) and the resulting suspension was stirred at ambient temperature for 16 hours. The reaction mixture was filtered, the filtrate diluted with EtOAc (200 mL), and washed with saturated brine (3×125 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)-2-hydroxyacetate (5.70 g, 92%) as a pale yellow oil which solidified on standing, which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate diluted with EtOAc (200 mL)
  3. washwashed with saturated brine (3×125 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-43398da6e19146bba0df727dbd9a353c
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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