Neopentyl glycol → HCID 20323933, compound

HRID 2083183Notes

Reaction equation

HRID 2083183 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[C:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1)([OH:10])=[O:9]>N1C=CC=CC=1>[CH3:1][C:2]([CH3:7])([CH2:5][O:6][C:15]([C:14]1[CH:18]=[CH:19][C:11]([C:8]([OH:10])=[O:9])=[CH:12][CH:13]=1)=[O:16])[CH2:3][O:4][C:15]([C:14]1[CH:18]=[CH:19][C:11]([C:8]([OH:10])=[O:9])=[CH:12][CH:13]=1)=[O:16]

Participants

4

Reactant 2

HCID 31344Neopentyl glycolHCID 123403414-(Chlorocarbonyl)benzoic acid

Product 1

HCID 20323933HCID 20323933, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mechanically stirred mixture of 15.6 g (0.15 M) of 2,2-dimethyl-1,3-propanediol, 92.25 g (0.5 M) of 4-carboxybenzoyl chloride and 500 ml of pyridine was refluxed under a nitrogen atmosphere. The resulting mixture was concentrated to dryness under reduced pressure, dispersed in 500 ml of distilled water, and acidified to pH 1 with concentrated hydrochloric acid. The precipitate was filtered off, washed three times with distilled water, and dried overnight at 100° C in a vacuum oven. The product was extracted for 5 days with 2 liters of hot benzene. The extract, on cooling, yielded 48.2 g of 4,4'-[(2,2-dimethyl -1,3-propanediyl)bis(oxycarbonyl)]bis(benzoic acid) melting at 287°-288° C. The infrared spectrum was consistent with the proposed structure and the compound was found to contain 5.13 meq of CO2H/g which corresponded to a molecular weight of 390 for the diacid.

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere
  2. concentrationThe resulting mixture was concentrated to dryness under reduced pressure
  3. additiondispersed in 500 ml of distilled water
  4. filtrationThe precipitate was filtered off
  5. washwashed three times with distilled water
  6. customdried overnight at 100° C in a vacuum oven
  7. extractionThe product was extracted for 5 days with 2 liters of hot benzene
  8. temperatureThe extract, on cooling

Sources & evidence

ORD record
ord-45199281a7b74b49b5877e5effa44a36
Source dataset
uspto-grants-1978_04
Patent number
US04085091

Reaction notes

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