Benzylsuccinic acid → 4-Oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 1765318Notes

Reaction equation

HRID 1765318 reaction equation
[CH2:1]([CH:8]([CH2:12][C:13]([OH:15])=O)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>S(=O)(=O)(O)O>[C:9]([CH:8]1[CH2:1][C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13](=[O:15])[CH2:12]1)([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 3858Benzylsuccinic acid

Product 1

HCID 2229644-Oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidYield 91.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-benzylsuccinic acid (78.37 g, 0.376 mol) in sulfuric acid (98%, 300 mL) was stirred at 60° C. for 20 min, then poured onto ice (2 kg), followed by extraction with diethyl ether (2 L, twice). The organic phase was washed with water, dried over anhydrous sodium sulfate, and evaporated under vacuum to obtain a solid. The solid was recrystallized from ethyl acetate to obtain the title compound (65.14 g, yield 91%). 1HNMR (DMSO-d6) δ 12.4–12.2 (bs, 1H), 7.80 (d, J=7.8 Hz, 1H), 7.50 (m, 1H), 7.34–7.28 (m, 2H), 3.21–3.07 (m, 3H), 2.73 (m, 2H). See also U.S. Pat. No. 5,739,135; J. Med. Chem. 1982, 25, 535–538; Org. Prep. Proc. Int. 1987, 19, 447–449.

Workup

  1. additionpoured onto ice (2 kg)
  2. extractionfollowed by extraction with diethyl ether (2 L
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under vacuum
  6. customto obtain a solid
  7. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-049a1fa0c53d4816bc98c35e67134c33
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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