Sulfuric Acid → 2-(carboxymethyl)-5-methoxybenzoic acid

HRID 2170126Notes

Reaction equation

HRID 2170126 reaction equation
[Cl-].[Cl-].[Ca+2].OS(O)(=O)=O.[CH3:9][O:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17]>>[C:16]([CH2:15][C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17])([OH:18])=[O:17]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 114613-Methoxybenzoic AcidHCID 5284359Calcium Chloride

Product 1

HCID 23054232-(carboxymethyl)-5-methoxybenzoic acidYield 164.4%

Procedure

A oven-dried 25 mL three neck round-bottomed flask containing a stirring bar was fitted with a drying tube (CaCl2) and charged with concentrated H2SO4 (12.0 mL). Dichlorovinyl)-5-methoxybenzoic acid (1.69 g, 6.83 mmol) was added portion wise to the stirred solution over 20 min. so that each additional portion was added only after the previous one was completely dissolved. After the addition was complete the reaction was left stirring at room temperature for 2 h and then it was poured onto ice. A precipitate formed and the mixture was stirred until the ice was dissolved. The precipitate was filtered, washed with cold water and dried to give 2-(carboxymethyl)-5-methoxybenzoic acid as an off-white solid (1.18 g, 82%). Spectral data for this compound were consistent with those in the literature. M.p. 175-177° C. (lit. m.p. 180-182° C.); 1H NMR (400 MHz, DMSO-d6): δ=12.36 (br. s, 2H), 7.39 (d, J=2.6 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.08 (dd, J=8.4 Hz, J=2.6 Hz, 1H), 3.84 (s, 2H), 3.78 (s, 3H).

Workup

  1. additionwas added only after the previous one
  2. dissolutionwas completely dissolved
  3. additionAfter the addition
  4. waitwas left
  5. additionit was poured onto ice
  6. customA precipitate formed
  7. dissolutionwas dissolved
  8. filtrationThe precipitate was filtered
  9. washwashed with cold water
  10. customdried

Sources & evidence

ORD record
ord-114ec931555145bd8404dc41f68cd5be
Source dataset
uspto-grants-2015_06
Patent number
US09050586B2

Reaction notes

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