Sodium Hydroxide → HCID 19004389, compound

HRID 2225835Notes

Reaction equation

HRID 2225835 reaction equation
C([O:3][C:4](=[O:32])[C:5](=[O:31])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[C:19]([O:26][CH3:27])[C:18]=2[CH2:28][CH2:29][CH3:30])=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([C:5](=[O:31])[C:4]([OH:32])=[O:3])=[CH:7][CH:8]=2)=[C:18]([CH2:28][CH2:29][CH3:30])[C:19]=1[O:26][CH3:27])(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67830530HCID 67830530, compound

Product 1

HCID 19004389HCID 19004389, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in example 10, a solution of 4-[3-[4-acetyl-3-methoxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.4 g) in methanol (30 mL) was treated with 2N sodium hydroxide (0.25 mL) was stirred at room temperature for 4 hours. Most of the solvents were removed in vacuo, water was added, then the mixture was acidified with 3N hydrochloric acid and extracted with dichloromethane-tetrahydrofuran (1:1). The dried (MgSO4) extracts were evaporated and the crude oil was purified by flash chromatography over silica gel (toluene-ethyl acetate-acetic acid; 75:25:0.5 increasing to 74:25:1) and crystallized from diethyl ether-hexane to provide 0.13 g of 4-[3-[4-acetyl-3-methoxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid, mp 94°-96° C.

Workup

  1. customMost of the solvents were removed in vacuo, water
  2. additionwas added
  3. extractionextracted with dichloromethane-tetrahydrofuran (1:1)
  4. dry with materialThe dried (MgSO4) extracts
  5. customwere evaporated
  6. customthe crude oil was purified by flash chromatography over silica gel (toluene-ethyl acetate-acetic acid; 75:25:0.5 increasing to 74:25:1)
  7. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-9bf633d5b85d4520b5994d064b3b92e2
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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