Diethyl Ether → 1,3-Diacetoxymethyl-5-[2-[1-(formylmethyl)cyclohexyl]ethoxy]benzene

HRID 2223911Notes

Reaction equation

HRID 2223911 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([O:17][CH2:18][CH2:19][C:20]2([CH2:26][CH2:27][OH:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:9]=[C:10]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[CH:11]=1)(=[O:3])[CH3:2].IC1C=CC=CC=1.C(O)(=O)C.C(O)(=O)C.C(OCC)C>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([O:17][CH2:18][CH2:19][C:20]2([CH2:26][CH:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:9]=[C:10]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12217721Iodo benzene diacetateHCID 597148422-[1-[2-(3,5-Diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol

Product 1

HCID 597148671,3-Diacetoxymethyl-5-[2-[1-(formylmethyl)cyclohexyl]ethoxy]benzeneYield 112%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-[2-(3,5-diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol (synthesized in Example 31) (430 mg) dissolved in dichloromethane (5 mL) were added diacetic acid iodobenzene (388 mg) and 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (18.5 mg) successively at room temperature. The solution was stirred for 15 hours. Diethyl ether was added to the solution and it was washed in turn with a 10% aqueous sodium thiosulfate solution, 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure to give the title compound (479 mg). This product was subjected to the subsequent step without further purification.

Workup

  1. washwas washed in turn with a 10% aqueous sodium thiosulfate solution, 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-d53b53f0c2a1433284284812a42b4bcb
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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