Sulfuric Acid → 1-(Spiro[4.5]dec-6-en-6-yl)ethanone

HRID 1471372Notes

Reaction equation

HRID 1471372 reaction equation
[C:1]([C:3]1[C:4]2([CH2:9][CH2:10][CH2:11][CH:12]=1)[CH2:8][CH2:7][CH2:6][CH2:5]2)#[CH:2].S(=O)(=O)(O)[OH:14].[OH-].[Na+]>C(O)(=O)C>[CH2:8]1[C:4]2([CH2:9][CH2:10][CH2:11][CH:12]=[C:3]2[C:1](=[O:14])[CH3:2])[CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 866475816-Ethynylspiro[4.5]dec-6-ene

Product 1

HCID 687258981-(Spiro[4.5]dec-6-en-6-yl)ethanoneYield 294.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 6-ethynylspiro[4.5]dec-6-ene (120 g, 0.748 mol) and sulfuric acid (11.6 g) in acetic acid (500 ml) was heated for 2 h at 75° C., poured into ice, treated with 2N aqueous NaOH (10 ml) and extracted twice with MTBE (150 ml). The combined organic phases were treated with 2N aqueous NaOH (pH>7), washed with water (400 ml), with a saturated aqueous solution of NaCl (400 ml), dried (MgSO4), and concentrated. Short-path Vigreux-distillation (0.08 mbar, head temperature: 85-90° C.) of the crude product (125 g) gave 1-(spiro[4.5]dec-6-en-6-yl)ethanone (62 g, 46%).

Workup

  1. additionpoured into ice
  2. extractionextracted twice with MTBE (150 ml)
  3. additionThe combined organic phases were treated with 2N aqueous NaOH (pH>7)
  4. washwashed with water (400 ml), with a saturated aqueous solution of NaCl (400 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. distillationShort-path Vigreux-distillation (0.08 mbar, head temperature: 85-90° C.) of the crude product (125 g)

Sources & evidence

ORD record
ord-0cee1b80d2a745739f52febc0a309278
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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