Benzene → HCID 19421674, compound

HRID 744098Notes

Reaction equation

HRID 744098 reaction equation
P(Cl)(Cl)(Cl)=O.C1C=CC=CC=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)(O)[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1>O>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([C:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=2)=[C:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 24813Phosphorus oxychlorideHCID 19421607Ethyl 3,3-bis(4-methoxyphenyl)-3-hydroxy-2-methylpropionate

Product 1

HCID 19421674HCID 19421674, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.10 ml of phosphorus oxychloride were dropped at from 5° to 10° C. onto 140 ml of a benzene solution containing 7.02 g of ethyl 3,3-bis(4-methoxyphenyl)-3-hydroxy-2-methylpropionate (prepared as described in Preparation 106) on an ice bath. The reaction solution was then stirred for 3 hours at room temperature, after which it was poured into water and then extracted with diethyl ether three times. The combined ethereal extracts were washed with a saturated aqueous solution of sodium bicarbonate, with water and with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure. The residue (6.72 g) was subjected to flash column chromatography through 100 g of silica gel. 6.04 g of the title compound were obtained as an oily substance from those fractions eluted with a 95:5 by volume mixture of hexane and ethyl acetate.

Workup

  1. extractionextracted with diethyl ether three times
  2. washThe combined ethereal extracts were washed with a saturated aqueous solution of sodium bicarbonate, with water and with a saturated aqueous solution of sodium chloride
  3. dry with materialafter which it was dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-a113696713b74212adc5f8484e89ebcb
Source dataset
uspto-grants-1996_09
Patent number
US05559109

Reaction notes

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