4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid → 4-(1,4-Dioxaspiro[4.5]decan-8-yl)benzoic acid

HRID 1016015Notes

Reaction equation

HRID 1016015 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:18][CH:19]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 595560954-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid

Product 1

HCID 299215764-(1,4-Dioxaspiro[4.5]decan-8-yl)benzoic acidYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5.3 g of 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid in 30 mL of methanol was added 2.3 g of Pd/C (10% wt). The suspension was stirred under H2 (balloon) for 1 h, filtered through celite pad and concentrated to dryness to give the desired product (5.2 g, yield: 97%) as a white solid: 1H NMR (CDCl3) δ 8.06-8.01 (2H, m), 7.58-7.53 (2H, m), 4.02 (4H, s), 2.73-2.67 (2H, m), 2.70-2.61 (1H, m), 1.93-1.64 (8H, m); MS: 262 (M+1)+.

Workup

  1. filtrationfiltered through celite pad
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d868278dab7c405da2308c7c493d41dc
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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