Acetic Acid → HCID 14880635, compound

HRID 487530Notes

Reaction equation

HRID 487530 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([NH:6][CH:7]2[O:11]CCO2)=[CH:4][CH:3]=1.[CH3:14][CH:15]1[CH2:20][CH2:19][C:18]2[C:21](OC(=O)[C:17]=2[CH2:16]1)=[O:22].O.[C:27](O)(=[O:29])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:6]2[C:7](=[O:11])[C:17]3[CH2:16][CH:15]([CH3:14])[CH2:20][CH2:19][C:18]=3[C:21]2=[O:22])=[CH:12][C:13]=1[CH:27]=[O:29]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1181314,5,6,7-Tetrahydro-5-methyl-1,3-isobenzofurandioneHCID 53706931HCID 53706931, compound

Product 1

HCID 14880635HCID 14880635, compoundYield 83%

Procedure

29.2 g (0.15 mol) of 4-chloro-(1,3-dioxolan-2-yl)-aniline and 24.9 g (0.15 mol) of 4(R,S)-methylcyclohexene-1,2-dicarboxylic anhydride were stirred in 250 ml of glacial acetic acid for 3 days at 230° C. and for 10 hours at 70° C.; water was added to induce precipitation, followed by recrystallization and drying. There was obtained 38 g (83%) of N-(4-chloro-3-formylphenyl)-4(R,S)-methyl-3,4,5,6-tetrahydrophthalimide (m.p. 132°-1330° C.).

Workup

  1. customprecipitation
  2. customfollowed by recrystallization
  3. customdrying

Sources & evidence

ORD record
ord-35cfd708aaef4239a4ac92634414857c
Source dataset
uspto-grants-1994_03
Patent number
US05296452

Reaction notes

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