Potassium Carbonate → Isohexane ethyl acetate

HRID 2281629Notes

Reaction equation

HRID 2281629 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>CN(C=O)C>[CH3:26][CH2:25][O:24][C:22]([CH3:21])=[O:23].[CH3:2][CH2:3][CH2:4][CH:5]([CH3:8])[CH3:6].[CH3:13][O:12][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 2

HCID 21882781Isohexane ethyl acetateHCID 67086798HCID 67086798, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of methyl 3-(4-hydroxyphenyl)propanoate (2 g, 11.10 mmol) in dry DMF (30 ml) at room temperature is added potassium carbonate (1.53 g, 11.10 mmol) followed by tert-butyl 2-bromoacetate (2.17 g, 11.10 mmol). The reaction mixture is purged with nitrogen, then stoppered and left stirring at room temperature for 7 days. The reaction mixture is poured into water (200 ml) and extracted with EtOAc (100 ml), washed with brine, dried (MgSO4), filtered and evaporated in vacuo to yield a pale yellow oil. Flash chromatography (SiO2, EtOAc/iso-hexane) yields 3-(4-tert-Butoxycarbonylmethoxy-phenyl)-propionic acid methyl ester as a clear oil.

Workup

  1. customThe reaction mixture is purged with nitrogen
  2. waitleft
  3. additionThe reaction mixture is poured into water (200 ml)
  4. extractionextracted with EtOAc (100 ml)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto yield a pale yellow oil

Sources & evidence

ORD record
ord-35a434e2178046229c18457ef6fd9720
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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