Toluene → HCID 86742905, compound

HRID 619874Notes

Reaction equation

HRID 619874 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]([OH:15])[C:13]#[CH:14])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](O)=[CH:19][CH:18]=1.[C:28]1(C)C=CC=CC=1>>[Cl:16][C:17]1[CH:18]=[C:19]2[C:20](=[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=13)[O:15][C:12]([CH3:28])([C:9]1[CH:10]=[CH:11][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:7][CH:8]=1)[CH:13]=[CH:14]2

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 117874-Chloro-1-naphtholHCID 56988094HCID 56988094, compound

Product 1

HCID 86742905HCID 86742905, compound

Procedure

A solution of p-pyrrolidinophenylpropargyl alcohol (2C) (5 g) and 4-chloro-1-naphthol (5 g) in toluene (75 cm3) was passed down a column of acidic alumina (100 g), using toluene as eluant. The colourless but heliochromic fraction (which turned blue on exposure to light from a flashgun) was evaporated and the residual solid recrystallised from acetone. The first crop of pure near colourless crystals was the benzochromene (4D; R=Cl).

Workup

  1. customwas evaporated
  2. customthe residual solid recrystallised from acetone

Sources & evidence

ORD record
ord-9875e4e34aa243a5afb0580cf052ba80
Source dataset
uspto-grants-1989_04
Patent number
US04818096

Reaction notes

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