Sodium Hydroxide → HCID 53837007, compound

HRID 2231902Notes

Reaction equation

C[O:2][C:3](=[O:37])[CH2:4][C:5]1([CH3:36])[CH2:10][CH2:9][C:8]2[C:11]([CH3:35])=[C:12]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=3[CH2:32][CH2:33][CH3:34])[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1.[OH-].[Na+]>>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][CH2:18][O:17][C:12]2[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]3[O:6][C:5]([CH3:36])([CH2:4][C:3]([OH:37])=[O:2])[CH2:10][CH2:9][C:8]=3[C:11]=2[CH3:35])=[C:23]([CH2:32][CH2:33][CH3:34])[C:24]=1[OH:31])(=[O:30])[CH3:29]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 54458671HCID 54458671, compound

Product 1

HCID 53837007HCID 53837007, compoundYield 59.6%

Procedure

A 0.669 g sample of the methyl ester from Example 20 was saponified with sodium hydroxide using the procedure described in Example 17. The crude acid product was chromatographed on 30 g of silica gel. Elution with 2:1 hexane-ethyl acetate afforded 0.386 g (59.6%) of racemic-6-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid as a yellow glass.

Workup

customThe crude acid product was chromatographed on 30 g of silica gel
washElution with 2:1 hexane-ethyl acetate

Sources & evidence

ORD record: ord-d65b8e6ce96f47008ccaa27a85a99e29
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04785017

Reaction notes

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