tert-Butanol → 51458-31-2

HRID 2281631Notes

Reaction equation

HRID 2281631 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C1CCN2C(=NCCC2)CC1.[C:36](O)([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C.O>[C:36]([O:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 1211242451458-31-2

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-(4-hydroxyphenyl)propanoic acid (3.32 g, 20 mmol) in dry DMF (20 ml) is carefully added 1,1′-carbonyldiimidazole (3.24 g, 20 mmol) portionwise. The reaction mixture is stirred at 40° C. for 2 hours after which time DBU (6.02 ml, 40 mmol) and tert-butanol (4.78 ml, 50 mmol) are added and the reaction mixture is now stirred at 65° C. for 2 days. The reaction mixture is allowed to cool to room temperature and poured into water (50 ml) and the product is extracted with diethyl ether (3×30 ml). The organics are combined, dried (MgSO4) and the solvent removed in vacuo to give a yellow oil. Purification by flash chromatography (SiO2, EtOAc/iso-hexane) yields 3-(4-Hydroxy-phenyl)-propionic acid tert-butyl ester as a colourless oil. 1H NMR (DMSO-d6) 9.1 (1H, s), 7.0 (2H, d, J=8.45), 6.65 (2H, d, J=8.45), 2.7 (2H, t, J=7.28), 2.4 (2H, t, J=7.28), 1.4 (9H, s).

Workup

  1. additionare added
  2. temperatureto cool to room temperature
  3. extractionthe product is extracted with diethyl ether (3×30 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a yellow oil
  7. customPurification by flash chromatography (SiO2, EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-a61f0f0e223d417b9dfcd96c4ba4f49b
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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