37470-83-0|5-Ethyl-2,4-dihydroxybenzaldehyde| Ambeed

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Quality Control of [ 37470-83-0 ] Purity: 95% SDS Specification

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Product Details of [ 37470-83-0 ]

CAS No. :	37470-83-0
Formula :	C₉H₁₀O₃
M.W :	166.17
SMILES Code :	O=CC1=CC(CC)=C(O)C=C1O
MDL No. :	MFCD21606577
InChI Key :	OMBGAXPPTGSSQZ-UHFFFAOYSA-N
Pubchem ID :	16088825

Safety of [ 37470-83-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340

Application In Synthesis of [ 37470-83-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 37470-83-0 ]

[ 37470-83-0 ] Synthesis Path-Downstream 1~40

1
[ 2896-60-8 ]
[ 74-90-8 ]
[ 37470-83-0 ]

References: [1]Journal of the Chemical Society,1934,p. 1491,1497.

2
[ 1190-39-2 ]
[ 37470-83-0 ]
6-ethyl-7-hydroxy-2-oxo-2<i>H</i>-chromene-3-carboxylic acid butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 1117,1121.

3
[ 37470-83-0 ]
[ 672936-83-3 ]

References: [1]Journal of the Chemical Society,1934,p. 1491,1497.

4
[ 37470-83-0 ]
[ 856106-66-6 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 22.
Chem.Abstr.,1950,p. 4444.

5
[ 37470-83-0 ]
5-ethyl-3-chloro-2,4-dihydroxy-benzaldehyde [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 90.
Chem.Abstr.,1950,p. 5330.

6
[ 37470-83-0 ]
[ 108-24-7 ]
[ 874516-43-5 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1951,vol. 71,p. 67.
Chem.Abstr.,1951,p. 8518.

7
[ 37470-83-0 ]
[ 119-26-6 ]
5-ethyl-2,4-dihydroxy-benzaldehyde-(2,4-dinitro-phenylhydrazone) [ No CAS ]

References: [1]Journal of the Chemical Society,1934,p. 1491,1497.

8
[ 37470-83-0 ]
[ 105-53-3 ]
[ 84165-75-3 ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 1117,1121.

9
[ 2896-60-8 ]
Zn(CN)2 [ No CAS ]
[ 37470-83-0 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 22.
Chem.Abstr.,1950,p. 4444.

10
[ 37470-83-0 ]
[ 107-30-2 ]
[ 913622-44-3 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.

11
[ 2896-60-8 ]
[ 33513-42-7 ]
[ 37470-83-0 ]

Yield	Reaction Conditions	Operation in experiment
62%		14.5 ml (0.18 mol) of dried dimethylformaldehyde was put in a 10 C. water bath and 4.43 ml (0.078 mol) of POCl3 was slowly added therein, followed by stirring for 30 minutes. 3.0 g (0.022 mol) of 4-ethylresorcinol was slowly added in 14.5 ml (0.18 mol) of dimethylformaldehyde, and the mixture was stirred at room temperature for 1 hour outside the water bath. The solution was put in a 0 C. water bath again and 2 M NaOH aqueous solution was added to quench the reaction. The reaction solution was diluted with ethyl acetate, followed by two times extraction with 2 M NaOH aqueous solution. The aqueous solution was neutralized by 3 N HCl, which was extracted four times by ethyl acetate and washed with brine. Combined organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated solution was purified by silica-gel column chromatography (hexane:ethyl acetate=7:1), to give 2.5 g of compound 2 (yield: 62%).
62%		Particularly, 14.5 ml (0.18 mol) of dried dimethylformaldehyde was put in a 10C water bath and 4.43 ml (0.078 mol) of POCl3 was slowly added therein, followed by stirring for 30 minutes. 3.0 g (0.022 mol) of A- ethylresorcinol was slowly added in 14.5 ml (0.18 mol) of dimethylformaldehyde, and the mixture was stirred at room temperature for 1 hour outside the water bath. The solution was put in a 0C water bath again and 2 M NaOH aqueous solution was added to quench the reaction. The reaction solution was diluted with ethyl acetate, followed by two times extraction with 2 M NaOH 'aqueous solution. The aqueous solution was 'neutralized by 3 N HCl, which was extracted four times' by ethyl acetate and washed, with brine. EPO <DP n="12"/>Combined organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated solution was purified by silica-gel column chromatography (hexane:ethyl acetate = 7:1), to give 2.5 g of compound 2 (yield: 62%).
36%		Dimethylformamide (38.2 mmol) and phosphorous oxychloride (43.1 mmol) were mixed at 0 C and stirred for 15 min before addition of 4-ethylbenzene-1,3-diol 6b (14.5 mmol) dissolved in dimethylformamide (10 mL). The mixture was heated to 80 C for 8 h. The reaction was quenched by the slow and careful addition of saturated aqueous sodium bicarbonate solution (150 mL) and was stirred overnight. The solution was extracted with CH2Cl2 (50 mL three times) and the combined organic layers were dried over Na2SO4. The pure product was isolated by flash column chromatography over silica gel (eluent: hexane/ethyl acetate gradient) and isolated as a white powder (yield 36.0%); Mp: 132 C (lit. mp: 130-131 CrefPreviewPlaceHolder48); IR (KBr) νmax: 1645.83 (-CO), 3193.79 (broad, -OH) cm-1; 1H NMR (400 MHz, DMSO-d6) δ 1.12 (t, 3H, CH3), 2.49 (q, 2H, CH2), 6.39 (s, 1H, ArH), 7.34 (s, 1H, ArH), 9.91 (s, 1H, CHO); 13C NMR (400 MHz, DMSO-d6) δ 13.92 (CH3), 21.76 (CH2), 101.79, 114.80, 122.98, 130.63, 161.44, 163.08 (ArC), 190.78 (CO); HRMS: C9H10O3 requires 167.0708; found 167.0711; Elemental Anal. C9H10O3 requires C, 65.05; H, 6.07. Found: C, 64.99; H, 6.07.

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.
[2]Patent: US2005/131036,2005,A1 .Location in patent: Page/Page column 3-4.
[3]Patent: WO2006/126751,2006,A1 .Location in patent: Page/Page column 10-11.
[4]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6055 - 6068.
[5]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3800 - 3802.
[6]Synthetic Communications,2012,vol. 42,p. 1890 - 1894.

12
[ 37470-83-0 ]
[ 913622-45-4 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.

13
[ 37470-83-0 ]
1-(3-formamido-2,5-dihydroxy-6-methoxyphenyl)propan-2-yl 5-ethyl-2,4-dihydroxybenzoate [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.

14
[ 37470-83-0 ]
[ 913622-47-6 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.

15
[ 37470-83-0 ]
1-(3-benzamido-2,5-dihydroxy-6-methoxyphenyl)propan-2-yl 5-ethyl-2,4-dihydroxybenzoate [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.

16
[ 37470-83-0 ]
[ 913622-46-5 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.

17
[ 37470-83-0 ]
[ 913622-48-7 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.

18
[ 37470-83-0 ]
[ 913622-49-8 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7618 - 7631.

Yield	Reaction Conditions	Operation in experiment
		A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at 0 C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethyresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100 mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1 N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1), 9.71(s,1), 7.29(s,1), 6.36(s(br),1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)
		A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at 0 C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethyresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100 mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1 N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1), 9.71(s,1), 7.29(s,1), 6.36(s(br),1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)
		A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at 0 C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethyresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100 mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1 N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1), 9.71(s,1), 7.29(s,1), 6.36(s(br), 1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)

		A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at 0 C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethyresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100 mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1 N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1)9.71(s,1)7.29(s,1) 6.36(s(br), 1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)
		A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at 0 C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethyresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100 mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1), 9.71(s,1), 7.29(s,1), 6.36(s(br), 1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)
		A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at 0 C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethyresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1), 9.71(s,1), 7.29 (s,1), 6.36(s(br),1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)
		STR13 Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at O C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethyresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100 mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1), 9.71(s,1), 7.29(s,1), 6.36(s(br),2), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)
		A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at 0 C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethyresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100 mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1 N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1), 9.71(s,1), 7.29(s,1), 6.36(s(br),1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)

20
[ 37470-83-0 ]
[ 74-88-4 ]
[ 76238-97-6 ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 5h;	2.55 g (0.015 mol) of the compound 2 and 4.24 g (0.03 mol) of potassium carbonate were dissolved in dimethylformaldehyde (25 ml). 2.28 g (0.016 mol) of methyl iodide was added therein, and the reaction mixture was stirred at room temperature for 5 hours. The reaction solution was filtered to remove inorganic salts, and 200 ml of water was added. Extraction was performed three times with ethyl acetate and then washed with brine. Combined organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated solution was purified by silica-gel column chromatography (hexane:ethyl acetate=20:1), to give 1.6 g of compound 3 (yield: 54%).
54%		2.55 g (0.015 mol) of the compound 2 and 4.24 g (0.03 mol) of potassium carbonate were dissolved in dimethylformaldehyde (25 ml). 2.28 g (0.016 mol) of methyl iodide was added therein, and the reaction mixture was stirred at room temperature for 5 hours. The reaction solution was filtered to remove inorganic salts, and 200 ml of water was added. Extraction was performed three times with ethyl acetate and then washed with brine. Combined organic layer was dried over anhydrous magnesium, sulfate, filtered, and concentrated under reduced pressure. The concentrated solution was purified by silica-gel column chromatography (hexane:ethyl acetate = 20:1), to give 1.6 g of compound 3 (yield: 54%).

References: [1]Patent: US2005/131036,2005,A1 .Location in patent: Page/Page column 4.
[2]Patent: WO2006/126751,2006,A1 .Location in patent: Page/Page column 10-11.
[3]Synthetic Communications,2012,vol. 42,p. 1890 - 1894.

21
chloronitrile [ No CAS ]
[ 37470-83-0 ]
[ 584-08-7 ]
[ 147527-86-4 ]

Yield	Reaction Conditions	Operation in experiment
38%	With Ki; In ethyl acetate; N,N-dimethyl-formamide;	B. Preparation of 1-[6-Methyl-6-cyanoheptyloxy]-2-ethyl-4-formyl-5-hydroxy benzene. To a mixture of 5-ethyl-2,4-dihydroxybenzaldehyde (10.05 g, 0.060 mol), K2 CO3 (14.63 g, 0.105 mol), KI (2.51 g, 0.015 mol) and DMF (250 mL), added a 250 mL solution of the chloronitrile (10.45 g, 0.060 mol) and warmed to 100 C. After 5 h, the reaction was cooled to room temp and the DMF was removed by vacuum distillation at 4 mmHg. The resulting brown oil was dissolved in EtOAc and washed with water and brine. The EtOAc extract was dried over MgSO4 and filtered. Solvent removal gave 17.0 g of a brown oil. The oil was purified by flash chromatography on silica gel eluding with 15% EtOAc/hexane. The desired product was obtained as a clear oil (6.98 g, 38%). TLC Rf=47 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.44(s,1), 9.67(s,1), 7.22(s,1), 6.36(s,1), 4.02(t,2,J=6.22 Hz), 2.56(q,2,J=7.52 Hz), 1.85(m,2), 1.55(s(br),6), 1.34(s,6), 1.18(t,3,J=7.50 Hz) IR(CHCl3) 2980, 2944, 2860, 2230, 1640, 1585, 1493 cm-1 Mass Spec(FD) m/e 303 (M+)

References: [1]Patent: US5352690,1994,A .

22
H₂ CO₃ [ No CAS ]
chloronitrile [ No CAS ]
[ 37470-83-0 ]
[ 147527-86-4 ]

Yield	Reaction Conditions	Operation in experiment
38%	With Ki; In ethyl acetate; N,N-dimethyl-formamide;	B. Preparation of 1-[6-Methyl-6-cyanoheptyloxy]-2-ethyl-4-formyl-5-hydroxy benzene. To a mixture of 5-ethyl-2,4-dihydroxybenzaldehyde (10.05 g, 0.060 mol), H2 CO3 (14.63 g, 0.105 mol), KI (2.51 g, 0.015 mol) and DMF (250 mL), added a 250 mL solution of the chloronitrile (10.45 g, 0.060 mol) and warmed to 100 C. After 5 h, the reaction was cooled to room temp and the DMF was removed by vacuum distillation at 4 mmHg. The resulting brown oil was dissolved in EtOAc and washed with water and brine. The EtOAc extract was dried over MgSO4 and filtered. Solvent removal gave 17.0 g of a brown oil. The oil was purified by flash chromatography on silica gel eluding with 15% EtOAc/hexane. The desired product was obtained as a clear oil (6.98 g, 38%). TLC Rf=47 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.44(s,1), 9.67(s,1), 7.22(s,1), 6.36(s,1), 4.02(t,2,J=6.22 Hz), 2.56(q,2,J=7.52 Hz), 1.85(m,2), 1.55(s(br), 6), 1.34(s,6), 1.18(t,3,J=7.50 Hz) IR (CHCl3) 2980, 2944, 2860, 2230, 1640, 1585, 1493 cm-1 Mass Spec(FD) m/e 303 (M+)

References: [1]Patent: US5352690,1994,A .

23
[ 2896-60-8 ]
dimethyformamide [ No CAS ]
[ 75-09-2 ]
[ 37470-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; trichlorophosphate; In water;	A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 mL) was cooled to 0 C. under argon atmosphere. With stirring, POCl3 (18.60 mL, 0.20 mol) was added slowly to the DMF. After several minutes at 0 C., the reaction was warmed to room temp and CH2 Cl2 (150 mL) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethylresorcinol (25.0 g, 0.181 mol) was added to the reaction mixture as a 200 mL CH2 Cl2 solution. After stirring at 0 C. for 10 min., the reaction was warmed to room temp and then refluxed for 16 h. The reaction was cooled to room temp, and a 100 mL water solution of NaOAc (50 g) was added slowly. This mixture was refluxed for 40 min then cooled to room temp. The aqueous layer was washed several times with CH2 Cl2. The organics were combined and washed with 1N HCl solution and brine the dried over MgSO4. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3)δ11.30(s,1), 9.71(s,1), 7.29(s,1), 6.36(s(br), 1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)

References: [1]Patent: US5352690,1994,A .

24
[ 2896-60-8 ]
dimethyformamide [ No CAS ]
[ 37470-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; trichlorophosphate; In dichloromethane; water;	A. Preparation of 5-Ethyl-2,4-Dihydroxybenzaldehyde. Dimethyformamide (250 ml) was cooled to 0 C. under argon atmosphere. With stirring, phosphorous oxychloride (18.60 ml, 0.20 mole) was added slowly to the N,N-dimethylformamide. After several minutes at 0 C., the reaction was warmed to room temperature and methylene chloride (150 ml) was added to the reaction mixture to dissolve the solid. The reaction was subsequently recooled to 0 C. 4-Ethylresorcinol (25.0 g, 0.181 mole) was added to the reaction mixture as a 200 ml methylene chloride solution. After stirring at 0 C. for 10 minutes., the reaction was warmed to room temperature and then refluxed for 16 h. The reaction was cooled to room temperature, and a 100 ml water solution of sodium acetate (50 g) was added slowly. This mixture was refluxed for 40 minutes then cooled to room temperature. The aqueous layer was washed several times with methylene chloride. The organics were combined and washed with 1N hydrochloric acid solution and brine the dried over magnesium sulfate. Filtration and solvent removal gave an orange solid which was recrystallized from toluene and hexane (17 g, 56%) TLC Rf=0.39 (30% EtOAc/Hexane) 1 H-NMR(CDCl3) δ11.30(s,1), 9.71(s,1), 7.29(s,1), 6.36(s(br),1), 2.61(q,2,J=7.48 Hz), 1.25(t,3,J=7.54 Hz)

References: [1]Patent: US5478857,1995,A .

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References: [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3800 - 3802.

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