3-Hydroxybenzoic Acid → HCID 53745704, compound

HRID 482314Notes

Reaction equation

HRID 482314 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Cl:11][CH2:12][CH2:13][CH2:14]O>S(=O)(=O)(O)O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:14][CH2:13][CH2:12][Cl:11])=[O:6]

Participants

4

Reactant 2

HCID 74203-Hydroxybenzoic AcidHCID 123133-Chloro-1-propanol

Product 1

HCID 53745704HCID 53745704, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-hydroxybenzoic acid (16.0 g, 0.115 mol) in 3-chloropropanol (76 g, 0.81 mol) and 0.5 mL of concentrated sulfuric acid was refluxed overnight. The excess alcohol was removed by vacuum distillation. The brown viscous residue was dissolved in ethyl acetate (60 mL) and washed with water (2×15 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The brown viscous residue was purified by column chromatography (ethyl acetate/hexane, 30:70) to give the product as a white solid (23.3 g, 0.108 mol, 93.7%): 1H NMR (CDCl3) δ2.19-2.28 (m, 2H), 3.69 (t, 2H, J=6.3 Hz), 4.48 (t, 2H, J=6Hz), 5.92 (s, 1H), 7.05-7.64 (m, 4H); MS exact mass: calcd. 214,0396, found 214.0400.

Workup

  1. customThe excess alcohol was removed by vacuum distillation
  2. dissolutionThe brown viscous residue was dissolved in ethyl acetate (60 mL)
  3. washwashed with water (2×15 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe brown viscous residue was purified by column chromatography (ethyl acetate/hexane, 30:70)

Sources & evidence

ORD record
ord-43df581430e741bdad4ad2f8438e2553
Source dataset
uspto-grants-1998_08
Patent number
US05795987

Reaction notes

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