Hydrochloric Acid → HCID 15044953, compound

HRID 654618Notes

Reaction equation

HRID 654618 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]([CH2:18][CH2:19][CH:20]([C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)[C:21]([O:23]C)=[O:22])[C:14]([O:16]C)=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[OH-].[K+].O.Cl>C(O)C>[CH3:32][O:31][C:29]1[CH:30]=[C:25]([CH:20]([CH2:19][CH2:18][CH:13]([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:14]([OH:16])=[O:15])[C:21]([OH:23])=[O:22])[CH:26]=[C:27]([O:35][CH3:36])[C:28]=1[O:33][CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 15044952HCID 15044952, compound

Product 1

HCID 15044953HCID 15044953, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of dimethyl α,α'-bis(3,4,5-trimethoxyphenyl)adipate (11.0 g, 21.7 mmoles), potassium hydroxide (13.0 g, 202 mmoles), water (163 ml), and ethanol (65 ml) was heated at 90° in a nitrogen atmosphere for 3 hours. After cooling the clear solution was added slowly to 250 ml of 1N hydrochloric acid with vigorous stirring. The slurry was stirred and warmed to 50° for several minutes. After cooling in an ice bath the solid was filtered, washed with water (4 times) and dried to give 10.07 g (97%) of α,α'-bis(3,4,5-trimethoxyphenyl)adipic acid, m.p. 226°-223°. NMR (DMSO-d6) indicates a 9:1 mixture of meso and racemic isomers.

Workup

  1. temperaturewas heated at 90° in a nitrogen atmosphere for 3 hours
  2. temperatureAfter cooling the clear solution
  3. temperaturewarmed to 50° for several minutes
  4. temperatureAfter cooling in an ice bath the solid
  5. filtrationwas filtered
  6. washwashed with water (4 times)
  7. customdried

Sources & evidence

ORD record
ord-4e392bab7b6c488f988e5327de4dc806
Source dataset
uspto-grants-1992_07
Patent number
US05132463

Reaction notes

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