Phenylacetic Acid → 4-(2-Mesyloxyethoxy)phenyl benzylketone

HRID 1738618Notes

Reaction equation

HRID 1738618 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:4])=[O:3].[C:15]1([CH2:21]C(O)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:25]1([CH:31]([CH2:35][CH3:36])[C:32](O)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[S:2]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:21]([C:32]([CH:31]([C:25]2[CH:30]=[CH:29][C:28]([O:8][CH2:7][CH2:6][O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:27][CH:26]=2)[C:35]2[CH:36]=[CH:11][CH:10]=[CH:9][CH:14]=2)=[O:33])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)([CH3:1])(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 999Phenylacetic AcidHCID 70122-Phenylbutyric AcidHCID 2264992-Phenoxyethyl methanesulfonate

Product 1

HCID 867545724-(2-Mesyloxyethoxy)phenyl benzylketoneYield 80%

Conditions

Temperature
25 °C

Procedure

The oil comprising 2-Phenoxyethyl methanesulfonate was prepared as described above in Example 1. The acylation and workup procedure was identical to that of Example 1 with the exception that 30.26 g (220 mmol) 2-phenylacetic acid was reacted instead of the 2-phenylbutyric acid. The organic layer obtained by the workup procedure was cooled to 25° C. and stirred at this temperature for 1 hour. The resulting crystallized product was filtered, washed with toluene and dried under vacuum at 40° C. to yield 53.18 g (159 mmol) of the 4-(2-mesyloxyethoxy)phenyl benzylketone as a tan colored solid. Yield: 80% on 2-phenoxyethanol.

Workup

  1. customwas prepared
  2. customThe organic layer obtained by the workup procedure
  3. customThe resulting crystallized product
  4. filtrationwas filtered
  5. washwashed with toluene
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-f59c121cca844a8bb94b070a82da3b2e
Source dataset
uspto-grants-1999_10
Patent number
US05962743

Reaction notes

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