3-Hydroxybenzaldehyde → tert-Butyl (3-formylphenoxy)acetate

HRID 2117608Notes

Reaction equation

HRID 2117608 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].CC(C)([O-])C.[K+].C(O)(C)(C)C.Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CN(C=O)C>[C:26]([O:25][C:23](=[O:24])[CH2:22][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6386tert-ButanolHCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14971816tert-Butyl (3-formylphenoxy)acetateYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxybenzaldehyde (5.00 g, 40.9 mmol) in DMF (40 mL) was added 1M potassium tert-butoxide in tert-butanol (40.9 mL, 40.9 mmol). The reaction was stirred for 2 minutes and tert-butyl bromoacetate (6.61 mL, 40.9 mmol) was added. The reaction was stirred for 1 hour and was quenched with 200 mL water. The product was extracted into EtOAc and the organic solution was washed with water, dried over MgSO4, filtered, and concentrated in vacuo. Purification via flash chromatography on silica gel (9:1 hexanes:EtOAc) afforded the title compound of Step A as a clear oil (3.53 g). 1H NMR (400 MHz, CDCl3) δ 9.94 (s, 1H), 7.48 (m, 2H), 7.32 (s, 1H) 7.21 (m, 1H), 4.56 (s, 2H), 1.45 (s, 9H).

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. customwas quenched with 200 mL water
  3. extractionThe product was extracted into EtOAc
  4. washthe organic solution was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification via flash chromatography on silica gel (9:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-c4ac1ea449c54590bd2182d359659e66
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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