Benzene → (1S)-1,2,3,4-Tetrahydronaphthalene-1-carboxylic acid

HRID 1901239Notes

Reaction equation

HRID 1901239 reaction equation
CO[C:3]1[CH:4]=[CH:5][C:6]2N=[CH:11][CH:10]=[C:9]([C@@H](O)[C@H]3N4C[C@H](C=C)[C@@H](CC4)C3)[C:7]=2[CH:8]=1.C1C=CC=CC=1.[C:31]([O:34]CC)(=[O:33])[CH3:32]>>[C@@H:32]1([C:31]([OH:34])=[O:33])[C:8]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 8857Ethyl AcetateHCID 3034034Quinine

Product 1

HCID 24820460(1S)-1,2,3,4-Tetrahydronaphthalene-1-carboxylic acid

Procedure

The quinine salt was suspended in 180 mL of ethyl acetate and the suspension was washed with 1N hydrochloric acid (2×92 mL). The mixture was then dried (NaSO4), filtered and concentrated. The residue was dissolved in hexane and crystallized to give (S)-1,2,3,4-tetrahydro-1-naphthoic acid (14.27 g 0.08 mol), m.p. 54°-56° C. [α]D -62.76° (c=1.0165, benzene).

Workup

  1. washthe suspension was washed with 1N hydrochloric acid (2×92 mL)
  2. dry with materialThe mixture was then dried (NaSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in hexane
  6. customcrystallized

Sources & evidence

ORD record
ord-9f6b82ba176743139d1ddcf4723a0870
Source dataset
uspto-grants-1996_11
Patent number
US05576434

Reaction notes

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