Water → Monomethyl terephthalate

HRID 345108Notes

Reaction equation

HRID 345108 reaction equation
S(=O)(=O)(O)O.[OH2:6].[CH3:7][O:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1>[O-2].[Cr+6].[O-2].[O-2].CC(C)=O>[CH3:7][O:8][C:9]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:6])=[O:17])=[CH:12][CH:11]=1)=[O:18]

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 81325Methyl 4-(hydroxymethyl)benzoate

Product 1

HCID 15513Monomethyl terephthalateYield 94%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

Concentrated sulfuric acid (277.5 ml, 5.2 mol) was added dropwise over 1/2 hr to a stirred solution of chromium (VI) oxide (299.25 g, 2.99 mol) and water (925 ml) at 0°. The resulting solution was added dropwise over 1 hr to a stirred solution of methyl-4-(hydroxymethyl)benzoate (92.5 g, 0.564 mol) and acetone (4.6 l) at 0°. The reaction mixture was allowed to warm to room temperature and stirred overnight The supernatant was decanted before the black tar-like residue was extracted with acetone. The decanted supernatant and acetone extracts were combined and concentrated under vacuum to leave a dark brown residue which was triturated with cold water (4 liter). The precipitate which formed was collected, washed three times with water (1 liter), and dried to give 94.6 g (94%) of the title compound as white crystals, m.p. 218°-221° C.

Workup

  1. customwas decanted before the black tar-like residue
  2. extractionwas extracted with acetone
  3. concentrationconcentrated under vacuum
  4. customto leave a dark brown residue which
  5. customwas triturated with cold water (4 liter)
  6. customThe precipitate which formed
  7. customwas collected
  8. washwashed three times with water (1 liter)
  9. customdried

Sources & evidence

ORD record
ord-b8a4803101984ccca32e68903f55759e
Source dataset
uspto-grants-1991_10
Patent number
US05055450

Reaction notes

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