Ethyl bromoacetate → (1-Hydroxy-2-benzyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid

HRID 597013Notes

Reaction equation

HRID 597013 reaction equation
[CH2:1]([C:8]1([CH3:21])[CH2:16][C:15]2[C:10](=[C:11]([Cl:19])[C:12]([Cl:18])=[C:13]([OH:17])[CH:14]=2)[CH:9]1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32]CC)=[O:31].[OH-].[Na+]>CN(C)C=O>[OH:20][CH:9]1[C:10]2[C:15](=[CH:14][C:13]([O:17][CH2:29][C:30]([OH:32])=[O:31])=[C:12]([Cl:18])[C:11]=2[Cl:19])[CH2:16][C:8]1([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:21]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 214494772-Benzyl-2-methyl-6,7-dichloro-1,5-indandiol

Product 1

HCID 21449480(1-Hydroxy-2-benzyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1-Hydroxy-2-benzyl-2methyl-6,7-dichloro-5-indanyloxy)acetic acid is prepared following subtantially the same procedure described in Example 4, Step F, using the following substances: 2-benzyl-2-methyl-6,7-dichloro-1,5indandiol (4.8 g., 0.015 mole); potassium carbonate (3.6 g.); ethyl bromoacetate (3.1 ml.); and dimethylformamide (35 ml.), and hydrolyzing the resultant ester with aqueous sodium hydroxide in accordance with Example 4, Step F, gives (1-hydroxy-2-benzyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid.

Workup

  1. custom(1-Hydroxy-2-benzyl-2methyl-6,7-dichloro-5-indanyloxy)acetic acid is prepared

Sources & evidence

ORD record
ord-bdeea8228d06440582b96c81e53123e5
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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