Potassium Bromide → Benzoic acid, 4,4'-carbonylbis-, dimethyl ester

HRID 1724112Notes

Reaction equation

HRID 1724112 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=2)[OH:23])=[CH:18][CH:17]=1)=[O:15].[K+].[Br-]>C(Cl)Cl>[CH3:33][O:32][C:30]([C:27]1[CH:26]=[CH:25][C:24]([C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17][CH:18]=2)=[O:23])=[CH:29][CH:28]=1)=[O:31]

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 14054779HCID 14054779, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 299003Benzoic acid, 4,4'-carbonylbis-, dimethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(Kirste, B.; Grimm, M.; Kurreck, H. J. Am. Chem. Soc. 1989, 111, 108-114.) To a suspension of PCC (3.10 g, 14.4 mmol) in anhydrous CH2Cl2 (25 ml) at RT, a solution of the benzyl alcohol 5 (2.70 g, 8.99 mmol) is added slowly dropwise into anhydrous CH2Cl2 (10 ml), and the preparation is stirred at this temperature over night. Subsequently, the mixture is filtered through a small amount of silica gel (CH2Cl2 as eluent). Following the distillation of the solvent, 2.44 g (91%) of compound 6 could be isolated in form of a colorless solid. Melting point 228-230° C. (Kirste et al. 1989, see above, 229.5-230° C.); IR (KBr) 1705, 1630 cm−1; 1H-NMR (CDCl3) δ 8.17 (d, 8.4 Hz, 4H), 7.85 (d, 8.4 Hz, 4H), 3.98 (s, 6H); MS (EI) m/z 298 (M+). Anal. calc. for C17H14O5: C, 68.45; H, 4.73. Found C, 68.30; H, 4.69.

Workup

  1. filtrationSubsequently, the mixture is filtered through a small amount of silica gel (CH2Cl2 as eluent)
  2. distillationthe distillation of the solvent, 2.44 g (91%) of compound 6
  3. customcould be isolated in form of a colorless solid
  4. customMelting point 228-230° C. (Kirste et al. 1989, see above, 229.5-230° C.)

Sources & evidence

ORD record
ord-f00fd5f9cdf649579cb58d9430aca814
Source dataset
uspto-grants-2009_02
Patent number
US07485742B2

Reaction notes

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