Water → HCID 19004460, compound

HRID 2225848Notes

Reaction equation

HRID 2225848 reaction equation
C([O:3][C:4](=[O:25])[C:5](=[O:24])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([CH:16]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:8][CH:7]=1)C.[OH-].[Na+].O>CO>[CH:16]1([C:14](=[O:15])[CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([C:5](=[O:24])[C:4]([OH:25])=[O:3])=[CH:7][CH:8]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54524851HCID 54524851, compound

Product 1

HCID 19004460HCID 19004460, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in example 19, a stirred solution of 4-(2-cyclooctyl-2-oxoethoxy)-alpha-oxobenzeneacetic acid ethyl ester (0.318 g) in warm methanol (5 mL) was treated with 1N sodium hydroxide (2 mL). Within 5 minutes water (20 mL) was added, then after the methanol was removed in vacuo, the mixture was acidified with 1N hydrochloric acid (2.5 mL) and extracted with dichloromethane (1×40 mL, 1×10 mL). The dried (MgSO4) extracts were evaporated and the resulting solid (0.255 g) was crystallized from diethyl ether-hexane to give 0.178 g of 4-[2-(cyclooctyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid as a colorless solid, mp 109°-110° C.

Workup

  1. customafter the methanol was removed in vacuo
  2. extractionextracted with dichloromethane (1×40 mL, 1×10 mL)
  3. dry with materialThe dried (MgSO4) extracts
  4. customwere evaporated
  5. customthe resulting solid (0.255 g) was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-723a9a50c0374f48ac532a35d3e2d736
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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