4-Hydroxybenzoic Acid → tert-Butyl 4-hydroxybenzoate

HRID 53271

Reaction equation

HRID 53271 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12](=[CH2:14])[CH3:13].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O1CCOCC1>[C:12]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1)([CH3:14])([CH3:13])[CH3:11]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium Bicarbonate

Product 1

HCID 117640tert-Butyl 4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-hydroxybenzoic acid (2.00 g, 14.5 mmol) in 1,4-dioxane (10.0 mL) saturated with isobutylene at -78° C. in a metal bomb was added concentrated sulfuric acid (0.150 mL). The bomb was sealed and warmed to room temperature. After 72 hours at room temperature, the reaction mixture was cooled to -78° C., poured into saturated sodium bicarbonate (30.0 mL) and extracted with diethyl ether (2×50.0 mL). The combined organic phases were concentrated and the residue chromatographed on silica gel (eluted with 5% methanol in methylene chloride to give 290 mg (Y: 10%) of the title product; 1H-NMR (CDCl3): δ7.89 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 1.57 (s, 9H).

Workup

  1. customThe bomb was sealed
  2. temperaturethe reaction mixture was cooled to -78° C.
  3. extractionextracted with diethyl ether (2×50.0 mL)
  4. concentrationThe combined organic phases were concentrated
  5. customthe residue chromatographed on silica gel (
  6. washeluted with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-a70620ce81214ac6a7dcb26b2b59ed24
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Linked notes

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