Cesium carbonate → 3-(2-(tert-Butoxy)-2-oxoethoxy)benzoic acid

HRID 277889Notes

Reaction equation

HRID 277889 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CN(C=O)C.CCOC(C)=O.[Pd]>[C:29]([O:28][C:26](=[O:27])[CH2:25][O:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 11736317Benzyl 3-hydroxybenzoate

Product 1

HCID 114140743-(2-(tert-Butoxy)-2-oxoethoxy)benzoic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To 7-2 (3.6 g, 16 mmol) in DMF (50 mL) was added Cs2CO3 (7.8 g, 238 mmol). After 15 min., tert-butyl bromoacetate (3.2 mL, 35 mmol) was added and the reaction mixture stirred for 20 hrs at ambient temperature. The reaction mixture was diluted with EtOAc and then washed with H2O, and brine, dried (MgSO4), and concentrated to give a yellow oil. The crude yellow oil (5.4 g, 15.8 mmol), 10% Pd/C (500 mg), and EtOAc (100 mL) was stirred under a hydrogen atmosphere (1 atm) for 20 hr. The reaction mixture was then filtered through a celite pad and the filtrate concentrated to give 7-3 as a white solid.

Workup

  1. washwashed with H2O, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give a yellow oil
  5. filtrationThe reaction mixture was then filtered through a celite pad
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ac772f43e7cb43d7898629e0d37715ff
Source dataset
uspto-grants-2002_03
Patent number
US06358970B1

Reaction notes

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