Sodium Hydroxide → HCID 12878296, compound

HRID 443937Notes

Reaction equation

HRID 443937 reaction equation
[OH:1][C:2]([CH3:27])([CH:9]=[CH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+].[Br:30]Br.C(=O)([O-])O.[Na+]>CO>[OH:1][C:2]1([CH3:27])[CH:9]([Br:30])[CH:10]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[O:6][C:4](=[O:5])[CH2:3]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 516892Sodium BicarbonateHCID 54152476HCID 54152476, compound

Product 1

HCID 12878296HCID 12878296, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The carboxylic acid (22.4 g) prepared by hydrolyzing 29.6 g of ethyl 3-hydroxy-3-methyl-7-(p-benzyloxyphenyl)-4-heptenoate with 80 ml of 4 N sodium hydroxide solution in 500 ml of methanol, was treated with 9.73 g of bromine in an aqueous sodium hydrogen carbonate solution and the reaction mixture was worked up according to the method described in Example 1 (b). The product was recrystallized from a mixture of n-hexane and acetone (10:1) to yield 13.5 g of the desired compound melting at 155°-160° C.

Workup

  1. customThe product was recrystallized from a mixture of n-hexane and acetone (10:1)

Sources & evidence

ORD record
ord-6a4b67bd420f4d5eb7c4641f6657d918
Source dataset
uspto-grants-1981_04
Patent number
US04262013

Reaction notes

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