Sulfuric Acid → HCID 178497878, compound

HRID 2081524Notes

Reaction equation

HRID 2081524 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH:16]=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.S(=O)(=O)(O)[OH:20].[C:24]1([CH3:30])C=CC=CC=1>>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH:16]3[O:20][CH2:24][CH2:30][O:17]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 178497880HCID 178497880, compound

Product 1

HCID 178497878HCID 178497878, compound

Procedure

A solution of 88.5 g of 4-(trans-4-formylcyclohexyl)benzoic acid methyl ester in 700 ml of toluene was treated while stirring with 1.5 ml of 10% (v/v) sulfuric acid and heated to boiling for 1 hour, with damp toluene being distilled off and being replaced by the addition of fresh toluene. Subsequently, the reaction solution was treated with 1 ml of triethylamine. The mixture was washed three times with 150 ml of water each time, dried over sodium sulfate, filtered and concentrated. Twofold recrystallization of the residue from tert. butyl methyl ether at -25° C. gave 75.4 g of pure 4-[trans-4-(1,3-dioxolan-2-yl) cyclohexyl]benzoic acid methyl ester with m.p. 110°-111° C.

Workup

  1. temperatureheated
  2. distillationdistilled off
  3. additionbeing replaced by the addition of fresh toluene
  4. additionSubsequently, the reaction solution was treated with 1 ml of triethylamine
  5. washThe mixture was washed three times with 150 ml of water each time
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customTwofold recrystallization of the residue from tert. butyl methyl ether at -25° C.

Sources & evidence

ORD record
ord-78b483a372d7417d804604dfe63bca1e
Source dataset
uspto-grants-1993_02
Patent number
US05185098

Reaction notes

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