Methanol → HCID 69338676, compound

HRID 1060790Notes

Reaction equation

HRID 1060790 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[C:17]([OH:19])=[O:18].[CH3:20]O>>[CH3:20][O:18][C:17]([C:9]1[CH:10]=[C:11]([C:12]([OH:14])=[O:13])[CH:15]=[CH:16][C:8]=1[O:7][CH3:6])=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 751524-Methoxyisophthalic acid

Product 1

HCID 69338676HCID 69338676, compound

Procedure

4-Methoxy-1,3-benzenedicarboxylic acid 3-monomethyl ester (formula 7) was prepared by adding at 20° C. under stirring 12 ml of concentrated sulphuric acid, d 1.84, to a suspension of 50 g of 4-methoxyisophthalic acid in 400 ml of methanol; stirring was then continued for 1 hour and then the mixture was poured into ice-water (400 ml). The precipitate was collected and stirred with a saturated solution of sodium hydrogen carbonate; the insoluble residue (15 g) was constituted by 4-methoxy-1,3-benzenedicarboxylic acid dimethyl ester. The filtered solution was adjusted to pH 4.8 by adding 6N hydrochloric acid, thus precipitating the desired monoester, which was collected and washed with water, yielding 28.1 g (52.5%) of white solid. By further acidification of the mother liquor unreacted 4-methoxy-1,3-benzenedicarboxylic acid (9 g) was precipitated and collected. In this way a total recovery of 44.2% was obtained by summing together the recovery of the acid and the dimethyl ester, thus allowing a useful yield of 96.7%.

Workup

  1. additionby adding at 20° C.
  2. customThe precipitate was collected
  3. stirringstirred with a saturated solution of sodium hydrogen carbonate
  4. additionby adding 6N hydrochloric acid
  5. customthus precipitating the desired monoester, which
  6. customwas collected
  7. washwashed with water

Sources & evidence

ORD record
ord-b68e6f435d564fa887d71510e6173a82
Source dataset
uspto-grants-2003_02
Patent number
US06525078B1

Reaction notes

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