Pivaloyl chloride → 4,4'-BIS(TRIMETHYLACETOXY)BENZOPHENONE

HRID 2119169Notes

Reaction equation

HRID 2119169 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:17][C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20]>N1C=CC=CC=1>[C:19]([O:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:19](=[O:20])[C:18]([CH3:23])([CH3:22])[CH3:17])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)(=[O:20])[C:18]([CH3:23])([CH3:22])[CH3:17]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 691504,4'-Dihydroxybenzophenone

Product 1

HCID 51137074,4'-BIS(TRIMETHYLACETOXY)BENZOPHENONE

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 10 g of 4,4'dihydroxybenzophenone in pyridine (40 ml) was treated with trimethylacetyl chloride and refluxed for 5 hours. The resultant solution was concentrated under reduced pressure and ETOAc added. The organic layer was washed with H2O, 5% aq. K2CO3, 1% aq. NaOH and dried over MgSO4 and concentrated to give approximately 13 g of a beige solid which was further chromatographed using 7/93 ethyl acetate-toluene to yield 2.83 g (20%) of the monoester (a) and 3.42 g (19%) (b) of the title compound; M.P.=166°-167° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. concentrationThe resultant solution was concentrated under reduced pressure and ETOAc
  3. additionadded
  4. washThe organic layer was washed with H2O, 5% aq. K2CO3, 1% aq. NaOH
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae2858f5414c43b79590a2fa0771e9cf
Source dataset
uspto-grants-1987_07
Patent number
US04683241

Reaction notes

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