Sulfuric Acid → 1285516-45-1

HRID 1623672Notes

Reaction equation

HRID 1623672 reaction equation
OS(O)(=O)=O.[C:6]1([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][C:15]=2[C:23]([OH:25])=[O:24])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:26]OC(C1C=CC(OCC2C=CC=CC=2)=C(C=1)C(O)=O)=O>CO>[CH3:26][O:24][C:23]([C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][C:14]=1[O:13][CH2:12][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:20]([OH:22])=[O:21])=[O:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 87068451,3-Benzenedicarboxylic acid, 4-(phenylmethoxy)-HCID 66722684HCID 66722684, compound

Product 1

HCID 671067771285516-45-1

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

H2SO4 (0.8 ml, 11.02 mmol) was added dropwise to a solution of 4-[(phenylmethyl)oxy]-1,3-benzenedicarboxylic acid (may be prepared as described in Description 48; 3 g, 11.02 mmol) in methanol (40 ml). The mixture was stirred at room temperature for 3 h before being poured into ice-water (40 ml). The precipitate was collected and added to a saturated NaHCO3 solution. The mixture was filtered to remove the insoluble residue and the pH of the filtrate was adjusted to pH=4.8 by HCl (6 mol/L). The precipitate was collected to afford crude product. The crude product was added to a silica gel column (300 g), and was eluted with dichloromethane/methanol=100:1 (3 L) to afford a mixture of 5-[(methyloxy)carbonyl]-2-[(phenylmethyl)oxy]benzoic acid and the title compound as a white solid. 1 g.

Workup

  1. customThe precipitate was collected
  2. additionadded to a saturated NaHCO3 solution
  3. filtrationThe mixture was filtered
  4. customto remove the insoluble residue
  5. customThe precipitate was collected
  6. customto afford crude product
  7. washwas eluted with dichloromethane/methanol=100:1 (3 L)
  8. customto afford

Sources & evidence

ORD record
ord-3e2775c761f04ab1abb4d0adcf9b945f
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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