Benzyl Chloride → HCID 67119827, compound

HRID 70006Notes

Reaction equation

HRID 70006 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[C:17]2[C:12](=[C:13]([OH:18])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:19]([OH:21])=[O:20].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([O:20][C:19]([C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]=1[O:7][CH2:19][C:9]1[CH:10]=[CH:11][CH:12]=[CH:17][CH:8]=1)=[O:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 538727221,5-Dihydroxy-naphthlene-2-carboxylic acid

Product 1

HCID 67119827HCID 67119827, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (2.45 g, 17.7 mmol), Dry DMF (5.4 mL), 1,5-Dihydroxy-naphthalene-2-carboxylic acid (0.539 g, 2.64 mmol), benzyl chloride (1.5 mL) Yield: 0.68 g of product (54%, 2 steps) Rf=0.38 (SiO2, 15% Hexanes/CH2Cl2). 1H NMR (400 MHz, CDCl3) δ 5.12 (s, 2H), δ 5.25 (s, 2H), δ 5.40 (s, 2H), δ 6.98 (d, J=7.3 Hz, 1H), δ 7.30-7.53 (m, 16H), δ 7.83 (d, J=8.7 Hz, 1H), δ 7.89 (d, J=8.7 Hz, 1H), δ 8.14 (d, J=8.7 Hz, 1H).

Sources & evidence

ORD record
ord-a8838e4c9271477f88911011941c5767
Source dataset
uspto-grants-2014_09
Patent number
US08822515B2

Reaction notes

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