Sodium Carbonate → 4-[6-[2,3-Bis-(phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acid

HRID 2225822Notes

Reaction equation

HRID 2225822 reaction equation
C([O:3][C:4](=[O:42])[C:5](=[O:41])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]=2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[C:35]1([CH2:34][O:33][C:20]2[C:21]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:9]2[CH:8]=[CH:7][C:6]([C:5](=[O:41])[C:4]([OH:42])=[O:3])=[CH:11][CH:10]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 544397754-[6-[2,3-Bis-(phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acid ethyl ester

Product 1

HCID 190043454-[6-[2,3-Bis-(phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acidYield 84.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-[6-[2,3-bis-(Phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acid ethyl ester (0.5 g) in methanol (50 mL) was treated with sodium carbonate (0.121 g) in water (2 mL), and the reaction was stirred at room temperature for 3 hours. After the solvents were removed in vacuo, dichloromethane and water were added and the mixture was acidified with 3N hydrochloric acid. The dried (Na2SO4) organic layer was evaporated to yield 0.4 g of 4-[6-[2,3-bis-(phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acid as an oil.

Workup

  1. customAfter the solvents were removed in vacuo, dichloromethane and water
  2. additionwere added
  3. dry with materialThe dried (Na2SO4) organic layer
  4. customwas evaporated

Sources & evidence

ORD record
ord-ea3ecef0decf4c1fbc44c1b52078ab57
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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