Hydrochloric Acid → 1-Naphthalenecarboxaldehyde, 5,6,7,8-tetrahydro-4-hydroxy-

5,6,7,8-Tetrahydro-naphthalen-1-ol (108, 20 g, 135 mmol) was stirred in 100 mL of ethanol, and potassium hydroxide (7.57 g, 135 mmol) as an aqueous solution was added. The mixture was stirred for 15 minutes and went clear. Solvents were removed and dried. PEG (MW 380-420, 53 mL) was added, followed by chloroform (32.3 mL, 405 mmol) and toluene (34 mL). An aqueous potassium hydroxide solution (50% by weight, 54.4 mL) was introduced dropwise with stirring over 15 minutes. The stirring was continued for another 30 minutes. 1M HCl was added to acidify the reaction mixture and it was extracted with EtOAc three times. The combined organic layers were washed with water and brine The combined organic layers were dried over MgSO4, filtered, concentrated, and purified by flash chromatography (0-40% EtOAc/hexane) to give 4-hydroxy-5,6,7,8-tetrahydro-naphthalene-1-carbaldehyde (109, 4.7 g).

1. customSolvents were removed
2. customdried
3. additionPEG (MW 380-420, 53 mL) was added
4. stirringwith stirring over 15 minutes
5. waitThe stirring was continued for another 30 minutes
6. extractionwas extracted with EtOAc three times
7. washThe combined organic layers were washed with water and brine The combined organic layers
8. dry with materialwere dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. custompurified by flash chromatography (0-40% EtOAc/hexane)

ORD record

ord-1a7a287f030748f496bd1e5ac41b02c6

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575176B2