Pivaloyl chloride → 2,4,4'-Tripivaloyloxybenzophenone

HRID 2119170Notes

Reaction equation

HRID 2119170 reaction equation
[OH:1][C:2]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)=[O:5].[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>N1C=CC=CC=1>[C:18]([O:1][C:2]1[CH:16]=[C:15]([O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:12][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:10][CH:11]=1)=[O:5])(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 738522,4,4'-Trihydroxybenzophenone

Product 1

HCID 140104022,4,4'-Tripivaloyloxybenzophenone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2.3 g (0.01 mole) of 2,4,4'trihydroxybenzophenone was warmed to 50° C. with 3.65 g (0.035 mole) of pivaloyl chloride in 75 mls of dry pyridine. After 2 hrs. at 5° C., the solvent was evaporated under N2 stream and H2O added to the residue. The oily material was extracted with CH2Cl2 and washed with dilute K2CO3. The organic layer was dried over MgSO4. The glass which was recovered after solvent removal was crystallized from ethanol; 4.20 g (86%) yield; M.P.~94°-96° C.

Workup

  1. customat 5° C., the solvent was evaporated under N2 stream and H2O
  2. additionadded to the residue
  3. extractionThe oily material was extracted with CH2Cl2
  4. washwashed with dilute K2CO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. customThe glass which was recovered
  7. customafter solvent removal
  8. customwas crystallized from ethanol
  9. custom4.20 g (86%) yield

Sources & evidence

ORD record
ord-6e738dac7e324a4f9001c1f968844b2c
Source dataset
uspto-grants-1987_07
Patent number
US04683241

Reaction notes

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