2,2',4,4'-Tetrahydroxybenzophenone → 2,2',4,4'-Tetra(3-methylvaleroyloxy)benzophenone

HRID 2119175Notes

Reaction equation

HRID 2119175 reaction equation
[OH:1][C:2]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[OH:13])=[O:5].[CH3:19][CH:20]([CH2:25][CH3:26])[CH2:21][C:22](Cl)=[O:23]>N1C=CC=CC=1>[CH3:19][CH:20]([CH2:25][CH3:26])[CH2:21][C:22]([O:1][C:2]1[CH:17]=[C:16]([O:18][C:22](=[O:23])[CH2:21][CH:20]([CH3:19])[CH2:25][CH3:26])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:22](=[O:23])[CH2:21][CH:20]([CH3:19])[CH2:25][CH3:26])=[CH:8][C:7]=1[O:13][C:22](=[O:23])[CH2:21][CH:20]([CH3:19])[CH2:25][CH3:26])=[O:5])=[O:23]

Participants

4

Reactant 2

HCID 85712,2',4,4'-TetrahydroxybenzophenoneHCID 126482793-Methylpentanoyl chloride

Product 1

HCID 140104012,2',4,4'-Tetra(3-methylvaleroyloxy)benzophenone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.2 g (0.005 mole) of 2,4,2',4'-tetrahydroxybenzophenone and 3 g (0.025 mole) of 3-methyl valeroylchloride was warmed to 50° C. for 4 hrs. in 50 mls of dry pyridine. Solvent removal via rotary evaporator left an oil. This was partitioned between H2O and CH2Cl2. The organic layer was washed with K2CO3 solution (5%) and dried over MgSO4. After filtration and solvent removal the product remained an oil; 2.5 g (78%) yield.

Workup

  1. customSolvent removal
  2. customvia rotary evaporator
  3. waitleft an oil
  4. customThis was partitioned between H2O and CH2Cl2
  5. washThe organic layer was washed with K2CO3 solution (5%)
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration and solvent removal the product
  8. custom2.5 g (78%) yield

Sources & evidence

ORD record
ord-e9b0e1d56ce04aedbdc25f7c3c6b18af
Source dataset
uspto-grants-1987_07
Patent number
US04683241

Reaction notes

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