Water → HCID 19004536, compound

HRID 2225840Notes

Reaction equation

HRID 2225840 reaction equation
C[O:2][C:3](=[O:28])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH:15]([OH:26])[C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[CH:7][CH:6]=1.[OH-].[Na+].O>CO>[OH:26][CH:15]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)[CH2:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:27])[C:3]([OH:28])=[O:2])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 53844584HCID 53844584, compound

Product 1

HCID 19004536HCID 19004536, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 19, a stirred solution of rac-4-[4-hydroxy-4-(2-naphthalenyl)butoxy]-alpha-oxobenzeneacetic acid methyl ester (0.172 g) in warm methanol (2.5 mL) was treated with 1N sodium hydroxide (1 mL) and then water (25 mL) was added. After the methanol was removed in vacuo, the mixture was acidified with 1N hydrochloric acid (1.2 mL) and extracted with dichloromethane (1×50 mL, 1×10 mL). The dried (MgSO4) extracts were concentrated and the residual gummy solid (~0.17 g) was crystallized from acetone-hexane to give 0.06 g of rac-4-[4-hydroxy-4-(2-naphthalenyl) butoxy]-alpha-oxobenzeneacetic acid as a colorless solid, mp 108°-110° C.

Workup

  1. customAfter the methanol was removed in vacuo
  2. extractionextracted with dichloromethane (1×50 mL, 1×10 mL)
  3. dry with materialThe dried (MgSO4) extracts
  4. concentrationwere concentrated
  5. customthe residual gummy solid (~0.17 g) was crystallized from acetone-hexane

Sources & evidence

ORD record
ord-125130008f6a4829a8f94446e2d184d8
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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