Methanol → HCID 15329251, compound

HRID 424028Notes

Reaction equation

HRID 424028 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:21])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CO.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:21])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6418291-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanoneHCID 4311764Sodium borohydride

Product 1

HCID 15329251HCID 15329251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g of precipitated 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone (1.74 mmol) prepared according to Example 4 are introduced into 75 ml of methanol and 62.5 ml of THF in a 250 ml three-necked round-bottomed flask. 0.78 g of sodium borohydride (1.1 eq.) is added at ambient temperature over approximately 1 h. The reaction medium is kept stirred for 1 h and concentrated and the residue is taken up in 50 ml of a water/methanol (50/50 by volume) mixture. The precipitate obtained is filtered off and washed on the filter with 25 ml of water/methanol (50/50 by volume). 5 g of a white precipitate are recovered, which precipitate, by NMR, corresponds to the expected 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanol, i.e. a virtually quantitative yield.

Workup

  1. concentrationconcentrated
  2. customThe precipitate obtained
  3. filtrationis filtered off
  4. washwashed on the
  5. filtrationfilter with 25 ml of water/methanol (50/50 by volume)
  6. custom5 g of a white precipitate are recovered
  7. customwhich precipitate, by NMR, corresponds to the expected 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanol, i.e. a virtually quantitative yield

Sources & evidence

ORD record
ord-ae32b8ccec0f4c0ea7b3e5688e6be381
Source dataset
uspto-grants-2012_01
Patent number
US08101804B2

Reaction notes

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