2-Hydroxy-4-methoxybenzophenone → HCID 16769077, compound

HRID 603360Notes

Reaction equation

HRID 603360 reaction equation
[BH4-].[Na+].[OH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>C(O)C.C1COCC1>[OH:13][CH:12]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:5]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=1[OH:3]

Participants

5

Reactant 2

HCID 46322-Hydroxy-4-methoxybenzophenoneHCID 4311764Sodium borohydride2×

Product 1

HCID 16769077HCID 16769077, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride is dissolved in 75 ml of ethanol, and the starting material (2-hydroxy-4-methoxyphenyl)phenylmethanone, dissolved in 5 ml of THF, is added dropwise over the course of about 10 min. The reaction mixture is stirred at room temperature for 1 h until all the sodium borohydride has been consumed. The solvent is removed in vacuo. The residue is partitioned in methyl t-butyl ether (MTBE)/water, and the aqueous phase is extracted a further 3 times with 50 ml of MTBE. The combined organic phases are dried over sodium sulfate, and the solvent is removed in vacuo.

Workup

  1. additionis added dropwise over the course of about 10 min
  2. customhas been consumed
  3. customThe solvent is removed in vacuo
  4. customThe residue is partitioned in methyl t-butyl ether (MTBE)/water
  5. extractionthe aqueous phase is extracted a further 3 times with 50 ml of MTBE
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-8ff70d2257c049ea9e2747dfa65c0496
Source dataset
uspto-grants-2011_03
Patent number
US07906684B2

Reaction notes

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