Water → HCID 67875437, compound

HRID 1497526Notes

Reaction equation

HRID 1497526 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](OCC2C=CC=CC=2)=[O:17])=[C:11]([Cl:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[C:11]([Cl:26])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 117787392HCID 117787392, compound

Product 1

HCID 67875437HCID 67875437, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl [4-(benzyloxy)-2-chlorophenyl]acetate (4.39 g) in tetrahydrofuran (80.0 mL) was added a 1 M solution of diisobutylaluminum hydride in toluene (37.0 mL) under ice-cooling under an argon atmosphere, followed by stirring for 1 hour under ice-cooling. To the reaction mixture was added a saturated aqueous Rochelle salt solution under ice-cooling. After stirring at room temperature for 2 hours, water was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 2-[4-(benzyloxy)-2-chlorophenyl]ethanol (3.01 g).

Workup

  1. temperaturecooling under an argon atmosphere
  2. temperaturecooling
  3. temperaturecooling
  4. stirringAfter stirring at room temperature for 2 hours
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-774a9c48743e4d7c83bc3fad4d53b7e8
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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