Water → Ethanone, 1-(3,5-bis(phenylmethoxy)phenyl)-

HRID 614120Notes

Reaction equation

HRID 614120 reaction equation
C[Li].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1)[C:14](O)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O1CCC[CH2:29]1.[OH2:33]>CCOCC>[CH3:29][C:14]([C:13]1[CH:12]=[C:11]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:17]=1)=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 993073,5-Bis(phenylmethoxy)benzoic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 120098Ethanone, 1-(3,5-bis(phenylmethoxy)phenyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Over a period of 1.5 hours, methyl lithium (531 ml. of a 2 molar solution, 1.06 M) is added under a nitrogen atmosphere to a rapidly stirring solution of 3,5-dibenzyloxybenzoic acid (175 g., 0.532 M) in ether (250 ml.) - tetrahydrofuran (1400 ml.) maintained at 15°-20° C. After stirring an additional 0.75 hour at 10°-15° C., water (600 ml.) is slowly added keeping the reaction temperature below 20° C. The aqueous layer is separated and extracted with ether (3 × 250 ml.). The organic phases are combined, washed with saturated sodium chloride solution (4 × 300 ml.), dried over sodium sulfate, and concentrated under vacuum to give an oil which slowly crystallized from isopropylether. The crude product is recrystallized from ether-hexane to yield 104.7 g. (59%) of product; m.p. 59°-61° C.

Workup

  1. temperaturemaintained at 15°-20° C
  2. customthe reaction temperature below 20° C
  3. customThe aqueous layer is separated
  4. extractionextracted with ether (3 × 250 ml.)
  5. washwashed with saturated sodium chloride solution (4 × 300 ml.)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customto give an oil which
  9. customslowly crystallized from isopropylether
  10. customThe crude product is recrystallized from ether-hexane
  11. customto yield 104.7 g

Sources & evidence

ORD record
ord-0678c11daacf45199467e5ec8dda7022
Source dataset
uspto-grants-1979_03
Patent number
US04143139

Reaction notes

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