(S)-6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-1-ol → (S)-5-hydroxy-5,6,7,8-tetrahydronapthalene-2-carbaldehyde

HRID 1431988Notes

Reaction equation

HRID 1431988 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]([OH:13])[CH2:8][CH2:7][CH2:6]2>C(Cl)Cl.CC#N.O=[Mn]=O>[OH:13][C@H:9]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:4]=[C:3]([CH:2]=[O:1])[CH:12]=[CH:11][C:10]1=2

Participants

4

Reactant 1

HCID 59771808(S)-6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 59771799(S)-5-hydroxy-5,6,7,8-tetrahydronapthalene-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a stirred solution of (S)-6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-1-ol (2.5 g, 14 mmol) in CH2Cl2/MeCN (1:1, 80 mL) was added MnO2 (6.1 g, 70. mmol). The reaction mixture was stirred for 16 h at RT. The solid was filtered off, and the filtrate was concentrated to afford the title compound. MS (m/z): 277.2 (M+H).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2ab2e40de1684374867fadc6612a25fb
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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