Acetic Anhydride → HCID 59289849, compound

HRID 1496835Notes

Reaction equation

HRID 1496835 reaction equation
O[C:2]1([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([OH:10])=[O:9].[Br:21]Br.[C:23]([O:26]C(=O)C)(=O)[CH3:24]>C(O)(=O)C>[C:23]([O:20][C:11]1([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:2]2([Br:21])[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7]2)[C:8](=[O:10])[O:9]1)(=[O:26])[CH3:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24408Bromine2×HCID 59289828HCID 59289828, compound

Product 1

HCID 59289849HCID 59289849, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

40 g (0.153 mol) of 2-hydroxy-2-(4-methoxy-benzoyl)-cyclohexanecarboxylic acid (=compound of example 6) are dissolved in 125 ml of acetic anhydride. 24.37 g (0.153 mol) of bromine in 24 ml of acetic acid are added slowly to this solution over 1 hour 40 minutes while keeping the temperature at 20° C. After addition of ⅓-½ equivalent of the bromine solution, a yellowish suspension is formed. The reaction mixture is stirred for 30 minutes at 20° C., followed by 1 hour at 0° C. in order to achieve complete precipitation of the product. The yellowish solid is filtered and washed with acetic acid anhydride to give 51 g (88%) 7a-bromo-1-(4-methoxy-phenyl)-3-oxo-octahydro-isobenzo-furan-1-yl acetate as a yellowish-white solid that is dried in vacuum at 40° C. and used for the next step without further purification.

Workup

  1. customat 20° C
  2. customa yellowish suspension is formed
  3. waitfollowed by 1 hour at 0° C. in order
  4. customprecipitation of the product
  5. filtrationThe yellowish solid is filtered
  6. washwashed with acetic acid anhydride

Sources & evidence

ORD record
ord-d01e6dcc435245088dc013a217db5d35
Source dataset
uspto-grants-2015_12
Patent number
US09199934B2

Reaction notes

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