Sodium Carbonate → Methyl 4-(2-formyl-6-pivaloyloxy-phenoxymethyl)benzoate

HRID 1739472Notes

Reaction equation

HRID 1739472 reaction equation
[OH:1][C:2]1[C:9]([O:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[Na+].[Na+].Br[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1>CN(C=O)C>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([O:10][C:11](=[O:16])[C:12]([CH3:13])([CH3:15])[CH3:14])[C:2]=1[O:1][CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 218410482-Hydroxy-3-pivaloyloxybenzaldehyde

Product 1

HCID 21840947Methyl 4-(2-formyl-6-pivaloyloxy-phenoxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-3-pivaloyloxybenzaldehyde (1.0 g, 4.5 mmole) in DMF (5 ml) was added Na2CO3 (0.859 g, 8.10 mmol) and methyl 4-bromomethylbenzoate (1.13 g, 4.93 mmol). The reaction was stirred at ambient temperature for 60 hours then partitioned between ethyl acetate/H2O. The organic phase was washed with water (x1) dried (MgSO4) and evaporated to give methyl 4-(2-formyl-6-pivaloyloxy-phenoxymethyl)benzoate as a product which was used in subsequent steps without further purification.

Workup

  1. customthen partitioned between ethyl acetate/H2O
  2. washThe organic phase was washed with water (x1)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-accd2920c5694c7cbdfd4c3bd27ed5d9
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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