Water → 3-Methyl-2-(naphthalen-2-yl)butanoic acid

HRID 2071324Notes

Reaction equation

HRID 2071324 reaction equation
[CH:1]([CH:4]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[C:5]#N)([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:18].[OH2:22]>>[CH:1]([CH:4]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[C:5]([OH:18])=[O:22])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 223937393-Methyl-2-(2-naphthyl)butyronitrile

Product 1

HCID 139522283-Methyl-2-(naphthalen-2-yl)butanoic acid

Conditions

Temperature
140 °C

Procedure

A mixture of α-isopropyl-2-naphthaleneacetonitrile (264.3 g, 1.263 mole), concentrated sulfuric acid (660 ml) and water (660 ml), is heated at 140° C. for 12 hours. The mixture is allowed to cool slowly during which the acid precipitates. The solid is collected by filtration, washed thoroughly with cold water (4 × 500 ml), and dried in a vacuum oven at 50° C. The yield is 281 g (97.6%). The solid is taken up in hexane (750 ml) and benzene (750 ml) and brought to boiling. The cloudy solution on cooling gives a white crystalline solid, which is collected and dried; (227 g, 2 crops, 78.8%); m.p. 129°-130° C. An analytical sample prepared in another run has a m.p. of 130°-131° C.

Workup

  1. temperatureto cool slowly during which the acid
  2. customprecipitates
  3. filtrationThe solid is collected by filtration
  4. washwashed thoroughly with cold water (4 × 500 ml)
  5. customdried in a vacuum oven at 50° C
  6. temperatureThe cloudy solution on cooling
  7. customgives a white crystalline solid, which
  8. customis collected
  9. customdried
  10. customAn analytical sample prepared in another run

Sources & evidence

ORD record
ord-a176699d243e4d1c9909715aa5b68864
Source dataset
uspto-grants-1977_09
Patent number
US04046799

Reaction notes

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