Trifluoroacetic acid → Methyl 4-(4-methoxyphenylmethyl)benzoate

HRID 1654718Notes

Reaction equation

HRID 1654718 reaction equation
[BH4-].[Na+].FC(F)(F)C(O)=O.[CH3:10][O:11][C:12]([C:14]1[CH:29]=[CH:28][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=O)=[CH:16][CH:15]=1)=[O:13]>C(Cl)Cl>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:18][C:17]2[CH:28]=[CH:29][C:14]([C:12]([O:11][CH3:10])=[O:13])=[CH:15][CH:16]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 257913Benzoic acid, 4-(4-methoxybenzoyl)-, methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 22408239Methyl 4-(4-methoxyphenylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of sodium borohydride (2.27 g) and trifluoroacetic acid (50 ml), which was previously prepared under nitrogen atmosphere, was added a solution of 4-methoxycarbonyl-4'-methoxybenzophenone (2.70 g) and methylene chloride (30 ml) at room temperature. After reacting for 24 hours, the reaction mixture was poured into ice-water, and methylene chloride layer was separated. Water layer was further extracted with methylene chloride (50 ml×2).

Workup

  1. customwas previously prepared under nitrogen atmosphere
  2. customwas separated
  3. extractionWater layer was further extracted with methylene chloride (50 ml×2)

Sources & evidence

ORD record
ord-4d253ce13825490aae1e4a35029f8374
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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