Sodium hydride → Pentanobenzeneacetic acid

HRID 1613576Notes

Reaction equation

HRID 1613576 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5])C.C1(=O)C2CCCCCC=2C=CC1.[H-].[Na+]>O1CCCC1>[C:7]1([CH2:6][C:4]([OH:5])=[O:3])[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21703317Benzocycloheptan-1-oneHCID 537587941-Ethoxycarbonylmethylbenzocycloheptane

Product 1

HCID 18918733Pentanobenzeneacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Benzocyclohept-1-en-1-yl)-acetic acid was prepared from 1-ethoxycarbonylmethylbenzocyclohept-1-ene, which was itself prepared from benzocycloheptan-1-one treated with ##STR11## and NaH in tetrahydrofuran, followed by separation of the two exocyclic unsaturated cis- and trans-isomers also formed, the separation being carried out by flash chromatography on silica gel with toluene as eluant.

Workup

  1. customfollowed by separation of the two exocyclic unsaturated cis- and trans-isomers
  2. customalso formed
  3. customthe separation

Sources & evidence

ORD record
ord-5c94360e4a7e40f3bb5d5ec38d85b435
Source dataset
uspto-grants-1993_03
Patent number
US05194437

Reaction notes

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