Ethanol → (2-Benzyloxy-5-methoxymethoxyphenyl)methanol

HRID 1294103Notes

Reaction equation

HRID 1294103 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][O:19][CH3:20])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.O1CCCC1.[BH4-].[Na+]>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][O:19][CH3:20])=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 178612512-Benzyloxy-5-methoxymethoxybenzaldehyde

Product 1

HCID 17861294(2-Benzyloxy-5-methoxymethoxyphenyl)methanolYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-benzyloxy-5-methoxymethoxybenzaldehyde (10.03 g), ethanol (50 mL) and tetrahydrofuran (100 mL) was added sodium tetrahydroborate (1.43 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give (2-benzyloxy-5-methoxymethoxyphenyl)methanol as a colorless oil (10.08 g, 97%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-216d3aabc43a42bf84ce93a06b49a3db
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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