Dichloromethane → 4-Dodecyloxybenzyl alcohol

HRID 2241852

Reaction equation

HRID 2241852 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24](OC)=[O:25])=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)Cl>C1COCC1>[CH2:7]([O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][OH:25])=[CH:28][CH:29]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 592397Methyl 4-(dodecyloxy)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 144776284-Dodecyloxybenzyl alcoholYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. slurry of LAH (13.0 g, 343 mmol) in dry THF (400 mL) was added slowly methyl 4-dodecyloxybenzoate (100 g, 312 mmol) in dry THF (350 mL) over 1.5 hours. Upon addition, the mixture was stirred at room temperature for one hour, after which TLC (CH2Cl2) showed completion. Reaction was cooled to 0° C. and quenched by successive addition of H2O (13 mL), 15% NaOH (13 mL), and H2O (39 mL), and stirring continued until H2 evolution ceased. Reaction mixture was then filtered and the lithium salts rinsed generously with CH2Cl2. The filtrate was dried over MgSO4 and concentrated to give the title benzyl alcohol (80 g, 88%), which was taken to the next step without further purification.

Workup

  1. additionUpon addition
  2. customReaction
  3. temperaturewas cooled to 0° C.
  4. customquenched by successive addition of H2O (13 mL), 15% NaOH (13 mL), and H2O (39 mL)
  5. stirringstirring
  6. customReaction mixture
  7. filtrationwas then filtered
  8. washthe lithium salts rinsed generously with CH2Cl2
  9. dry with materialThe filtrate was dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bd6f67588d84496dbd22e926be13980a
Source dataset
uspto-grants-2010_03
Patent number
US07671033B2

Linked notes

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