4-Hydroxybenzaldehyde → HCID 44136568, compound

HRID 1876293Notes

Reaction equation

HRID 1876293 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[SH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17]O.Cl>ClCCl>[S:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][O:7][CH:6]1[C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 1382782-Mercaptobenzenemethanol

Product 1

HCID 44136568HCID 44136568, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the same procedure as outlined in Example 1 step b), 4-hydroxybenzaldehyde (0.73 g, 5.95 mmol) and (2-mercaptophenyl)methanol (1 g, 7.14 mmol) in dichloromethane (30 ml) were treated with hydrogen chloride gas. After workup and chromatography, as in example 1 step b), the subtitle compound was obtained (0.91 g, 63%) as a white solid. 1H NMR (300 MHz, CDCl3, ppm) δ 5.04 (d, J=15 Hz, 1H); 5.10 (d, J=15 Hz, 1H); 5.19 (s, 1H); 6.02 (s, 1H); 6.76-6.81 (m, 2H); 6.96-7.03 (m, 1H); 7.04-7.19 (m, 3H); 7.35-7.42 (m, 2H): 13C NMR (75 MHz, CDCl3, ppm) δ 70.6; 82.8; 115.7; 125.1; 126.0, 127.5; 128.4; 129.9; 130.6; 133.1; 156.4; MS calculated for C14H12O2S+H 245 observed 245.

Sources & evidence

ORD record
ord-c8f20f946ff245578f0f0e7343a5d4a4
Source dataset
uspto-grants-2012_11
Patent number
US08309598B2

Reaction notes

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