4-Hydroxybenzoic Acid → Benzyl 4-Hydroxybenzoate

HRID 635562Notes

Reaction equation

HRID 635562 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11](OC(=NC(C)C)NC(C)C)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 11128254o-Benzyl-n,n'-diisopropylisourea

Product 1

HCID 7180Benzyl 4-Hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A neat solution of 18.6 mL (15g, 118.8 mmol) of 1,3-diisopropylcarbodiimide and 60 mg (0.6 mmol) of cuprous chloride was placed under a blanket of argon and then cooled to 0° C. in an ice bath. To this reaction mixture was added dropwise (via syringe) 12.9 mL (13.5 g, 124.7 mmol) of benzyl alcohol. The resultant green reaction mixture was allowed to stir at 0° C. overnight, filtered through celite (rinsing with hexane) and the filtrate then Kugelrohr distilled (105° C., 2 mm Hg) to give 2-benzyl-1,3-diisopropyl isourea as a clear, colorless oil. To a solution of 650 mg (4.7 mmol) of 4-hydroxybenzoic acid in 20 mL of tetrahydrofuran was added 1.1 g (4.7 mmol) of 2-benzyl-1,3-diisopropyl isourea. The reaction mixture was allowed to stir at ambient temperature overnight, filtered (rinsing with tetrahydrofuran) and then concentrated in vacuo. Purification by flash chromatography (silica, 25% ethyl acetate in hexane) gave the title compound as a white solid. PMR (CDCl3): δ 5.22 (1 H, s), 5.35 (2 H, s), 6.87 (2 H, d, J=8.8 Hz), 7.34-7.50 (5 H, m), 8.01 (2 H, d, J=8.8 Hz).

Workup

  1. filtrationfiltered
  2. wash(rinsing with tetrahydrofuran)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography (silica, 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-274c392a62ac48b5bae0939cf48e2bdf
Source dataset
uspto-grants-2001_02
Patent number
US06187950B1

Reaction notes

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