Hydrochloric Acid → 1-(2,3-dihydro-1H-inden-6-yl)cyclopropanecarboxylic acid

HRID 1991876Notes

Reaction equation

HRID 1991876 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]3([C:13]#N)[CH2:12][CH2:11]3)[CH:8]=2)[CH2:3][CH2:2]1.[OH-:15].[Na+].Cl.C[OH:19]>>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]3([C:13]([OH:19])=[O:15])[CH2:12][CH2:11]3)[CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 591295421-(2,3-dihydro-1H-inden-6-yl)cyclopropanecarbonitrile

Product 1

HCID 591293901-(2,3-dihydro-1H-inden-6-yl)cyclopropanecarboxylic acidYield 47%

Conditions

Temperature
100 °C

Procedure

To a stirred 1-(2,3-dihydro-1H-inden-6-yl)cyclopropanecarbonitrile (9.3 g, 50.8 mmol) in methanol (40 mL) was added a solution of 150 mL of sodium hydroxide (25% NaOH w/w in water). The mixture was heated at 100° C. for 8 hours. After cooling to room temperature, the reaction mixture was poured over ice-water (0° C.), the pH was adjusted to pH=4 with hydrogen chloride (1 N) and the mixture was extracted with dichloromethane (3×100 mL). The combined organic layers were dried over Na2SO4 and evaporated under vacuum. The residue that was purified by column chromatography (petroleum ether:ethyl acetate=5:1) to give 1-(2,3-dihydro-1H-inden-6-yl)cyclopropanecarboxylic acid (4.8 g, 47%). 1H NMR (CDCl3, 400 MHz) δ 1.23-1.26 (m, 2H), 1.62-1.65 (m, 2H), 2.03-210 (m, 2H), 2.81-2.91 (m, 4H), 7.11-7.21 (m, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with dichloromethane (3×100 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated under vacuum
  5. customThe residue that was purified by column chromatography (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-4e8c4c133b7d4be3902b7fc94a566ae2
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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