Ethanol → Benzoic acid, 3,5-dihydroxy-, ethyl ester

HRID 1868569Notes

Reaction equation

HRID 1868569 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[K+].[Br-].[CH2:19](O)[CH3:20]>>[CH2:19]([O:6][C:5](=[O:7])[C:4]1[CH:3]=[C:2]([OH:1])[CH:10]=[C:9]([OH:11])[CH:8]=1)[CH3:20]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 74243,5-Dihydroxybenzoic AcidHCID 253877Potassium Bromide

Product 1

HCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl ester

Procedure

To a solution of 3,5-dihydroxy benzoic acid, 1 (19 g, 123 mmol) in dry ethanol (250 mL) was added 2-3 mL of concentrated sulphuric acid drop wise and refluxed for 8 h. Ethanol was evaporated on rotavapor, diluted with water and extracted with ether. Combined ethereal layers were again washed with saturated sodium bicarbonate solution, water and dried over sodium sulphate, filtered and evaporated to dryness to afford 3. Yield 16.8 g (75%); mp 128-130° C.; MS (FAB) 183 (M++1); IR (KBr) 3496, 1819, 1687; 1H NMR (200 MHz, DMSO-d6) δ 9.89 (s, 2H), 7.06 (d, J=2.2 Hz, 2H), 6.69 (t, J=2.2 Hz, 1H), 4.48 (q, J=7.1 Hz, 2H), 1.52 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturerefluxed for 8 h
  2. customEthanol was evaporated on rotavapor
  3. additiondiluted with water
  4. extractionextracted with ether
  5. washwere again washed with saturated sodium bicarbonate solution, water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto afford 3

Sources & evidence

ORD record
ord-a97059a8c0ba4091aa4b70fd91699b76
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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