2-Chloroethanol → 2-Chloroethyl 3-hydroxybenzoate

HRID 964820Notes

Reaction equation

HRID 964820 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]O>S(=O)(=O)(O)O.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:13][CH2:12][Cl:11])=[O:6]

Participants

5

Reactant 2

HCID 342-ChloroethanolHCID 74203-Hydroxybenzoic Acid

Product 1

HCID 151587912-Chloroethyl 3-hydroxybenzoateYield 95.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

##STR32## A solution of 3-hydroxybenzoic acid (15.0 g, 0.11 mol) in 2-chloroethanol (70 mL, 1.0 mol) and 1 mL of concentrated sulfuric acid was refluxed for overnight. TLC analysis (silica gel/20% ethyl acetate/hexane) showed clean conversion to a new material. The excess chloroethanol was removed by evaporation to obtain a brown solution which -was dissolved in ethyl acetate and washed with water. The organic layer was dried with MgSO4 and concentrated to obtain 21.0 g of the product as a white solid: mp 50° C.; 1H NMR (CDCl3) δ 3.81 (t, 2H, J=5.9 Hz), 4.57 (t, 2H, J=5.9 Hz), 4.77 (s, 1H), 7.06-7.66 (m, 4H), 13C NMR (CDCl3) δ 41.52, 64.75, 116.43, 120.77, 121.98, 129.80, 130.71, 156.04, 166.57; MS m/e (rel. intensity) 200 (26), 138 (59), 121 (100), 93 (31), 65 (21), 39 (12); MS exact mass; calcd. 200.0240, found 200.0242.

Workup

  1. customThe excess chloroethanol was removed by evaporation
  2. customto obtain a brown solution which
  3. washwashed with water
  4. dry with materialThe organic layer was dried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a85f7bd1892843d0a6b9a7793cc65b09
Source dataset
uspto-grants-1998_06
Patent number
US05770743

Reaction notes

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