Diisopropyl Ether → (3-methoxy-4-methylphenyl)methanol

HRID 1374993Notes

Reaction equation

HRID 1374993 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=1[C:9](O)=O.[BH4-].[Na+].[B].C([O:19]C(C)C)(C)C>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[CH3:9])[CH2:12][OH:19]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 5971642-Methoxy-4-methylbenzoic acidHCID 4311764Sodium borohydrideHCID 5462311Boron

Product 1

HCID 11744818(3-methoxy-4-methylphenyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-methoxy-p-toluic acid (45.32 g) in tetrahydrofuran (280 ml) was added to a suspension of sodium borohydride (9.29 g) in tetrahydrofuran (45 ml) with ice bath cooling under nitrogen atmosphere. After 10 minutes stirring, boron trifuluoride diethyl etherate (41.5 ml) was added to the mixture at 3 to 15° C. and the whole was stirred at room temperature overnight. Water (210 ml) and diisopropyl ether (60 ml) were added to the mixture. The organic layer was separated and the aqueous layer was extracted with diisopropyl ether (100 ml). The combined organic layer was washed successively with 1N sodium hydroxide solution and brine, dried over sodium sulfate, and evaporated in vacuo to give 3-methoxy-4-methylbenzylalcohol (41.63 g) as an oil.

Workup

  1. temperaturecooling under nitrogen atmosphere
  2. stirringthe whole was stirred at room temperature overnight
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with diisopropyl ether (100 ml)
  5. washThe combined organic layer was washed successively with 1N sodium hydroxide solution and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0e7d7a21a9264f86ace7ff2698ee528b
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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