Water → HCID 54204827, compound

HRID 1065651Notes

Reaction equation

HRID 1065651 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5](O)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[CH2:6][CH2:7][CH3:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.OS(O)(=O)=O.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 54444434HCID 54444434, compound

Product 1

HCID 54204827HCID 54204827, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 58.9 g of 3-hydroxy-3-(o-tolyl)-hexanoic acid methyl ester, 1.1 g p-toluene sulphonic acid and 2.5 ml concentrated H2SO4 in 400 ml toluene is boiled in a water separator under reflux. The resultant reaction solution is concentrated, taken up in CHCl3, washed with NaHCO3 solution, H2O and then NaCl solution and then concentrated. The crude product in CHCl3 is filtered through silica gel and the filtrate concentrated. The product containing 3-(o-tolyl)-hex-2-and/or 3-enoic acid methyl ester is taken up in 400 ml methanol and hydrogenated in the presence of 2.1 g 10% (by weight) Palladium on charcoal at 20° and at 1.1 atmospheres to yield 3-o-tolyl-hexanoic acid methyl ester, which is further worked up as such.

Workup

  1. temperatureunder reflux
  2. customThe resultant reaction solution
  3. concentrationis concentrated
  4. washwashed with NaHCO3 solution, H2O
  5. concentrationNaCl solution and then concentrated
  6. filtrationThe crude product in CHCl3 is filtered through silica gel
  7. concentrationthe filtrate concentrated
  8. additionThe product containing 3-(o-tolyl)-hex-2-and/or 3-enoic acid methyl ester
  9. customis taken up in 400 ml methanol and hydrogenated in the presence of 2.1 g 10% (by weight) Palladium on charcoal at 20° and at 1.1 atmospheres

Sources & evidence

ORD record
ord-3e681a67e70f401eaec19d105b9fad9f
Source dataset
uspto-grants-1982_05
Patent number
US04330555

Reaction notes

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