Water → HCID 24974018, compound

HRID 1364001Notes

Reaction equation

HRID 1364001 reaction equation
COC([C:5]1[CH2:10][CH2:9][C:8]2([CH2:15][CH2:14][CH2:13][CH:12]=[CH:11]2)[CH2:7][C:6]=1[OH:16])=O.[Na+].[Cl-].O>CS(C)=O>[CH2:7]1[C:8]2([CH2:15][CH2:14][CH2:13][CH:12]=[CH:11]2)[CH2:9][CH2:10][CH2:5][C:6]1=[O:16]

Participants

5

Reactant 3

HCID 962Water2×HCID 5234Sodium ChlorideHCID 66936618HCID 66936618, compound

Product 1

HCID 24974018HCID 24974018, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of the relevant 2-hydroxy-spiro[5.5]undecan-2,7-diene-3-carboxylic acid methyl ester isomer (9) or (9′) (19.0 g, 85.0 mmol) in DMSO (66 mL) was added NaCl (5.5 g, 93.5 mmol) and H2O (4.6 mL, 255 mmol). The reaction mixture was heated at 160° C. for 6 hours then cooled and poured into H2O (100 mL). The aqueous layer was extracted with Et2O (5×) and the combined organic layers dried over anhydrous MgSO4. The solvent was removed in vacuo and the resulting residue purified over silica (n-pentane/Et2O, 95:5) to afford 13.3 g (95% yield) of the desired product as a colorless oil which was characterized as follows:

Workup

  1. temperaturethen cooled
  2. extractionThe aqueous layer was extracted with Et2O (5×)
  3. dry with materialthe combined organic layers dried over anhydrous MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe resulting residue purified over silica (n-pentane/Et2O, 95:5)

Sources & evidence

ORD record
ord-61e755aaafc84a8c80a2b01096a56c71
Source dataset
uspto-grants-2011_02
Patent number
US07888338B2

Reaction notes

Loading…